Would You Rather Questions to Boost Real Estate Investing Engagement

Frustrated with sparking fun, meaningful engagement in your real estate investing community? Would You Rather questions are a playful way to get members sharing their opinions and experiences. Use these imaginative templates to drive participation and lively discussions.

Real Estate Investing 41 Templates

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Why This Works

Would You Rather posts tap into curiosity and imagination, prompting members to compare two interesting scenarios. This format lowers the barrier to participation, since members only have to choose between two options, making it easy for everyone to join in.

The playful nature of these questions encourages creative thinking and lets members share their reasoning, revealing insights about their investing style and preferences. Over time, these discussions help build camaraderie, encourage new voices, and keep community conversations fresh and dynamic.

41 Ready-to-Use Templates

1

Would you rather flip a single high-end property or multiple budget homes this year?

πŸ’‘ Example: "Would you rather flip a single high-end property or multiple budget homes this year?"

🟑 Medium Engagement Barrier πŸ‘€ Average #strategy #flipping
2

Would you rather invest in a city you know well or take a chance on an emerging market?

πŸ’‘ Example: "Would you rather invest in a city you know well or take a chance on an emerging market?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #market #risk
3

Would you rather manage tenants yourself or hire a property management company? Tell us why.

πŸ’‘ Example: "Would you rather manage tenants yourself or hire a property management company? Tell us why."

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #management #discussion
4

Would you rather have a portfolio of single-family homes or a few multifamily units?

πŸ’‘ Example: "Would you rather have a portfolio of single-family homes or a few multifamily units?"

🟑 Medium Engagement Barrier πŸ‘€ Average #portfolio #units
5

Would you rather invest in short-term rentals or long-term leases? Why?

πŸ’‘ Example: "Would you rather invest in short-term rentals or long-term leases? Why?"

πŸ”΄ High Engagement Barrier πŸ‘€ Top #rentals #strategy
6

Would you rather buy a fixer-upper at a discount or pay more for a turnkey property?

πŸ’‘ Example: "Would you rather buy a fixer-upper at a discount or pay more for a turnkey property?"

🟑 Medium Engagement Barrier πŸ‘€ Average #fixer-upper #turnkey
7

Would you rather partner up with another investor or go it alone for your next deal?

πŸ’‘ Example: "Would you rather partner up with another investor or go it alone for your next deal?"

🟑 Medium Engagement Barrier πŸ‘€ Average #partnership #solo
8

Would you rather have a property in a bustling city or a quiet rural area? Share your choice.

πŸ’‘ Example: "Would you rather have a property in a bustling city or a quiet rural area? Share your choice."

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #location #preference
9

Would you rather find deals through networking or online listings?

πŸ’‘ Example: "Would you rather find deals through networking or online listings?"

🟒 Low Engagement Barrier πŸ‘€ Lurker #deals #sourcing
10

Would you rather take a big risk for high returns or play it safe with steady cash flow?

πŸ’‘ Example: "Would you rather take a big risk for high returns or play it safe with steady cash flow?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #risk #returns
11

Would you rather own one luxury property or several small rental units?

πŸ’‘ Example: "Would you rather own one luxury property or several small rental units?"

🟑 Medium Engagement Barrier πŸ‘€ Average #luxury #rental
12

Would you rather renovate an old historic building or build new from scratch? Why?

πŸ’‘ Example: "Would you rather renovate an old historic building or build new from scratch? Why?"

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #renovation #development
13

Would you rather own commercial properties or stick to residential real estate?

πŸ’‘ Example: "Would you rather own commercial properties or stick to residential real estate?"

🟑 Medium Engagement Barrier πŸ‘€ Average #commercial #residential
14

Would you rather buy in your home country or invest internationally?

πŸ’‘ Example: "Would you rather buy in your home country or invest internationally?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #international #domestic
15

Would you rather secure a loan with a low interest rate or flexible terms? Explain your pick.

πŸ’‘ Example: "Would you rather secure a loan with a low interest rate or flexible terms? Explain your pick."

πŸ”΄ High Engagement Barrier πŸ‘€ Top #financing #loans
16

Would you rather have consistent but small monthly profits or occasional big windfalls?

πŸ’‘ Example: "Would you rather have consistent but small monthly profits or occasional big windfalls?"

🟑 Medium Engagement Barrier πŸ‘€ Average #profits #cash flow
17

Would you rather deal with a fixer-upper disaster or a problem tenant? Which is easier for you?

πŸ’‘ Example: "Would you rather deal with a fixer-upper disaster or a problem tenant? Which is easier for you?"

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #challenges #problems
18

Would you rather attend a real estate conference or take an online investing course?

πŸ’‘ Example: "Would you rather attend a real estate conference or take an online investing course?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #education #learning
19

Would you rather invest in new developments or established neighborhoods? Why?

πŸ’‘ Example: "Would you rather invest in new developments or established neighborhoods? Why?"

πŸ”΄ High Engagement Barrier πŸ‘€ Top #developments #neighborhoods
20

Would you rather have a hands-on role or be a passive investor in your next deal?

πŸ’‘ Example: "Would you rather have a hands-on role or be a passive investor in your next deal?"

🟑 Medium Engagement Barrier πŸ‘€ Average #active #passive
21

Would you rather inherit a property with lots of issues or buy a ready-to-rent unit?

πŸ’‘ Example: "Would you rather inherit a property with lots of issues or buy a ready-to-rent unit?"

🟑 Medium Engagement Barrier πŸ‘€ Average #inherit #ready-to-rent
22

Would you rather work with a mentor or learn by trial and error?

πŸ’‘ Example: "Would you rather work with a mentor or learn by trial and error?"

🟒 Low Engagement Barrier πŸ‘€ Lurker #mentorship #learning
23

Would you rather buy at auction or through a traditional agent? Share your reasons.

πŸ’‘ Example: "Would you rather buy at auction or through a traditional agent? Share your reasons."

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #auction #agent
24

Would you rather focus on cash flow or appreciation in your investment strategy?

πŸ’‘ Example: "Would you rather focus on cash flow or appreciation in your investment strategy?"

🟑 Medium Engagement Barrier πŸ‘€ Average #cash flow #appreciation
25

Would you rather own property in a vacation hotspot or in a business district?

πŸ’‘ Example: "Would you rather own property in a vacation hotspot or in a business district?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #location #vacation
26

Would you rather have one long-term tenant or several short-term guests each year?

πŸ’‘ Example: "Would you rather have one long-term tenant or several short-term guests each year?"

🟑 Medium Engagement Barrier πŸ‘€ Average #tenants #short-term
27

Would you rather invest in a property with high appreciation or high rental yield?

πŸ’‘ Example: "Would you rather invest in a property with high appreciation or high rental yield?"

🟑 Medium Engagement Barrier πŸ‘€ Average #yield #appreciation
28

Would you rather buy a small multifamily building or several single-family homes?

πŸ’‘ Example: "Would you rather buy a small multifamily building or several single-family homes?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #multifamily #single-family
29

Would you rather renovate kitchens or bathrooms for higher ROI? Why?

πŸ’‘ Example: "Would you rather renovate kitchens or bathrooms for higher ROI? Why?"

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #renovation #ROI
30

Would you rather be known for finding hidden gems or closing lightning-fast deals?

πŸ’‘ Example: "Would you rather be known for finding hidden gems or closing lightning-fast deals?"

🟑 Medium Engagement Barrier πŸ‘€ Average #reputation #deals
31

Would you rather invest with friends or keep business and friendship separate?

πŸ’‘ Example: "Would you rather invest with friends or keep business and friendship separate?"

🟒 Low Engagement Barrier πŸ‘€ Lurker #friends #business
32

Would you rather own a property with a pool or with a huge backyard? What is your pick?

πŸ’‘ Example: "Would you rather own a property with a pool or with a huge backyard? What is your pick?"

πŸ”΄ High Engagement Barrier πŸ‘€ Frequent #features #preference
33

Would you rather have full control of all decisions or delegate most tasks?

πŸ’‘ Example: "Would you rather have full control of all decisions or delegate most tasks?"

🟑 Medium Engagement Barrier πŸ‘€ Average #control #delegation
34

Would you rather invest in properties near schools or near public transport?

πŸ’‘ Example: "Would you rather invest in properties near schools or near public transport?"

🟑 Medium Engagement Barrier πŸ‘€ Average #location #schools
35

Would you rather buy in a buyer's market or sell in a seller's market? Tell us why.

πŸ’‘ Example: "Would you rather buy in a buyer's market or sell in a seller's market? Tell us why."

πŸ”΄ High Engagement Barrier πŸ‘€ Top #market #timing
36

Would you rather use your own money or raise capital from investors?

πŸ’‘ Example: "Would you rather use your own money or raise capital from investors?"

🟑 Medium Engagement Barrier πŸ‘€ Average #capital #funding
37

Would you rather have a property with smart tech features or classic charm?

πŸ’‘ Example: "Would you rather have a property with smart tech features or classic charm?"

🟑 Medium Engagement Barrier πŸ‘€ Average #tech #classic
38

Would you rather spend more on marketing or on renovations for your next listing?

πŸ’‘ Example: "Would you rather spend more on marketing or on renovations for your next listing?"

🟑 Medium Engagement Barrier πŸ‘€ Irregular #marketing #renovation
39

Would you rather own a penthouse in the city or a farmhouse on the outskirts?

πŸ’‘ Example: "Would you rather own a penthouse in the city or a farmhouse on the outskirts?"

🟑 Medium Engagement Barrier πŸ‘€ Average #penthouse #farmhouse
40

Would you rather have a tenant who pays late but stays for years or one who pays on time but moves out often?

πŸ’‘ Example: "Would you rather have a tenant who pays late but stays for years or one who pays on time but moves out often?"

πŸ”΄ High Engagement Barrier πŸ‘€ Top #tenants #payment
41

Would you rather buy a property sight unseen or only after multiple visits?

πŸ’‘ Example: "Would you rather buy a property sight unseen or only after multiple visits?"

🟑 Medium Engagement Barrier πŸ‘€ Average #buying #sight unseen

How to Use These Templates

Pick a template that fits your group's mood or topical focus, then post it as a new discussion or as a story/poll. Encourage members to reply with their choice and the reasons behind it. Consider tagging or mentioning members to spark responses. You can also use these as icebreakers in onboarding, or as regular engagement rituals to keep your community lively.

Best Practices

  • Keep scenarios relevant to real estate investing but fun and light-hearted.
  • Encourage members to explain their reasoning, not just pick an option.
  • Rotate topics between beginner and advanced investing situations.
  • Monitor responses to avoid controversial or overly complex debates.
  • Use member replies as a springboard for deeper follow-up discussions.

All Platforms Tips

For all platforms, keep your Would You Rather questions concise and visually clear. Use line breaks or bolding to separate the two options. On forums or Facebook, pin the question for greater visibility. On chat-based platforms, use these to kick off daily threads or quick polls. Always acknowledge and respond to member answers to encourage more engagement.

Frequently Asked Questions

How can I tailor 'Would You Rather' questions to engage both residential and commercial real estate investors?

To maximize engagement across your audience, alternate between scenarios relevant to both segments. For example, pose questions like 'Would you rather renovate a single-family rental or reposition an office building?' or 'Would you prefer to invest in multifamily properties in emerging markets or retail centers in established neighborhoods?' This approach sparks discussion among investors with different specialties while exposing them to new perspectives.

Is it better to focus 'Would You Rather' questions on acquisition strategies (like BRRRR vs. fix-and-flip) or on financing methods (such as hard money loans vs. JV partnerships)?

Mixing acquisition strategies and financing methods keeps content fresh and appeals to investors at different stages. For example, 'Would you rather finance your next deal with a hard money loan or bring in a joint venture partner?' or 'Would you rather build wealth through the BRRRR method or stick to traditional fix-and-flip projects?' Rotating between these themes ensures all members find questions relevant to their interests.

How do I create 'Would You Rather' questions that address unique market challenges, like rising interest rates or supply shortages?

Develop questions around current market conditions to spark timely discussions. For instance, 'Would you rather lock in a higher fixed-rate mortgage now or wait and risk prices increasing further?' or 'Would you rather invest in new construction despite supply shortages or focus on value-add properties during this period?' This shows your community you’re in touch with real-world investing challenges.

What are some examples of 'Would You Rather' scenarios that highlight the trade-offs between passive vs. active investing in real estate?

You can ask, 'Would you rather be a limited partner in a large multifamily syndication or self-manage a small portfolio of single-family rentals?' or 'Would you rather earn lower returns with less involvement or take on more risk and time for higher potential gains?' These questions help members reflect on where they fit within the active-passive spectrum and encourage knowledge sharing.

How can I use 'Would You Rather' questions to spark discussions about geographical diversification, like investing locally versus out-of-state?

Craft questions such as, 'Would you rather invest in your local market, where you know the neighborhoods, or diversify by buying properties in a different state with better cash flow?' or 'Would you rather own one high-value property close to home or several lower-priced properties across different markets?' These scenarios invite members to share experiences and strategies for managing risk through diversification.

Should I include 'Would You Rather' questions that focus on exit strategies, such as holding for cash flow versus flipping for immediate profit?

Absolutely. Exit strategy dilemmas are central to real estate investing. Ask questions like, 'Would you rather hold a property for long-term rental income or sell quickly for a lump sum profit?' or 'Would you rather 1031 exchange into a bigger asset or cash out and diversify into other investments?' These spark meaningful discussions on risk tolerance, return expectations, and long-term goals.

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