Battle-Tested Would You Rather Prompts for Flipping Real Estate Communities

Struggling to spark fun and thoughtful discussions in your flipping real estate community? Would You Rather questions are the perfect way to fuel creativity and bring members together. This template library provides engaging prompts designed to get everyone talking and sharing their perspectives.

Flipping Real Estate 42 Templates

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Why This Works

Would You Rather questions tap into the natural human love of choice and imagination. By presenting two intriguing scenarios, you invite members to picture themselves in each situation, which helps them engage on a personal level. This format is playful yet insightful, lowering barriers to participation and making it easy for even quieter members to jump in.

In a flipping real estate community, these questions encourage members to share their unique experiences, preferences, and creative approaches. The format is simple to understand and answer, yet it can uncover deeper insights into how your audience thinks about risk, opportunity, and deal-making. Overall, Would You Rather posts generate lively discussions and foster a sense of camaraderie among members.

42 Ready-to-Use Templates

1

Would you rather flip a historic house with hidden surprises or a brand new build with strict HOA rules?

💡 Example: "I would pick the historic house - surprises can be tough, but the charm is unbeatable!"

🔴 High Engagement Barrier 👤 Average #historic #HOA #choices
2

Would you rather find a deal with a low purchase price but high rehab costs, or a higher price with minimal repairs needed?

💡 Example: "Minimal repairs for me, less stress and a quicker turnaround."

🟡 Medium Engagement Barrier 👤 Average #budget #strategy #repairs
3

Would you rather flip one luxury property per year or multiple starter homes in the same timeframe?

💡 Example: "Multiple starter homes - more deals and less risk if one flops!"

🟡 Medium Engagement Barrier 👤 Frequent #luxury #starter homes #scale
4

Would you rather work with a partner who brings funding or one who brings construction expertise?

💡 Example: "Construction expertise is gold for me, funding is easier to source."

🟡 Medium Engagement Barrier 👤 Average #partnership #funding #skills
5

Would you rather flip a house in your own city or try your luck in a new, unfamiliar market?

💡 Example: "I love the idea of new markets - more opportunities to learn."

🟡 Medium Engagement Barrier 👤 Irregular #local #remote #market
6

Would you rather have a tight deadline with a big bonus for early completion, or a flexible timeline but a smaller profit?

💡 Example: "Big bonus for me, I thrive under pressure!"

🔴 High Engagement Barrier 👤 Top #deadline #profit #motivation
7

Would you rather renovate kitchens or bathrooms in every flip?

💡 Example: "Bathrooms are my favorite - smaller space, big impact."

🟢 Low Engagement Barrier 👤 Lurker #kitchen #bathroom #design
8

Would you rather DIY all the painting or hire out for a flawless finish?

💡 Example: "I always hire out for painting - saves me time and stress."

🟢 Low Engagement Barrier 👤 Lurker #DIY #contractors #painting
9

Would you rather deal with a stubborn seller or a picky buyer?

💡 Example: "Stubborn sellers - once the deal is done, it is done!"

🟡 Medium Engagement Barrier 👤 Average #negotiation #buyers #sellers
10

Would you rather flip a property with foundation issues or a bad roof?

💡 Example: "Roof every time, foundation problems can get out of hand."

🔴 High Engagement Barrier 👤 Frequent #repairs #risk #major issues
11

Would you rather stage a home yourself or use a professional staging service?

💡 Example: "Professional staging is worth the investment for me."

🟢 Low Engagement Barrier 👤 Average #staging #presentation #marketing
12

Would you rather have a flip with amazing curb appeal but dated interiors, or stunning interiors but a bland exterior?

💡 Example: "Stunning interiors - buyers spend more time inside!"

🟡 Medium Engagement Barrier 👤 Irregular #curb appeal #interior #design
13

Would you rather get a great deal at auction or through a private seller?

💡 Example: "Private seller deals are usually less stressful for me."

🟢 Low Engagement Barrier 👤 Lurker #auction #private sale #deal sourcing
14

Would you rather flip a single-family home or a duplex?

💡 Example: "Duplexes are my go-to - two opportunities in one!"

🟢 Low Engagement Barrier 👤 Average #property type #duplex #single-family
15

Would you rather focus on cosmetic updates or full gut renovations?

💡 Example: "Cosmetic updates for faster turns and less risk."

🟡 Medium Engagement Barrier 👤 Average #cosmetic #gut reno #strategy
16

Would you rather flip a property in a hot market or buy low in a slower area?

💡 Example: "I prefer slower markets - less competition and better deals."

🟡 Medium Engagement Barrier 👤 Frequent #market #hot #slow
17

Would you rather have unlimited capital or a team of expert contractors for your flipping business?

💡 Example: "Expert contractors - the money follows great execution!"

🔴 High Engagement Barrier 👤 Top #capital #team #resources
18

Would you rather flip a home with a pool or one with a big backyard?

💡 Example: "Big backyard - more buyers want space for kids and pets."

🟢 Low Engagement Barrier 👤 Lurker #amenities #pool #yard
19

Would you rather try a flip in a rural area or stick to the suburbs?

💡 Example: "Suburbs for me - rural flips are too unpredictable."

🟡 Medium Engagement Barrier 👤 Irregular #rural #suburban #market
20

Would you rather manage your own flip or hire a project manager?

💡 Example: "Project manager all the way - frees me up for more deals."

🟡 Medium Engagement Barrier 👤 Average #management #project manager #DIY
21

Would you rather have a property that needs extensive landscaping or one that needs a new kitchen?

💡 Example: "Landscaping is less intrusive - easier to schedule."

🟡 Medium Engagement Barrier 👤 Average #landscaping #kitchen #repairs
22

Would you rather flip a house with great bones but outdated everything, or a modern house with structural issues?

💡 Example: "Great bones - structure is the hardest thing to fix."

🔴 High Engagement Barrier 👤 Top #bones #modern #issues
23

Would you rather take a risk on a property with a mysterious history or one with lots of paperwork hurdles?

💡 Example: "Paperwork hurdles - I like to know what I am getting into."

🟡 Medium Engagement Barrier 👤 Frequent #risk #history #paperwork
24

Would you rather flip a condo or a townhouse?

💡 Example: "Townhouse for sure - fewer HOA headaches."

🟢 Low Engagement Barrier 👤 Lurker #property type #condo #townhouse
25

Would you rather invest in a flip for short-term profit or as a long-term rental?

💡 Example: "Long-term rental - love that steady income."

🟡 Medium Engagement Barrier 👤 Average #investment #profit #rental
26

Would you rather flip a property with a unique layout or a cookie-cutter home?

💡 Example: "Unique layout - stands out in the market!"

🟡 Medium Engagement Barrier 👤 Irregular #layout #unique #cookie-cutter
27

Would you rather handle all the paperwork yourself or pay a pro to do it?

💡 Example: "Pay a pro - time is money in this business."

🟢 Low Engagement Barrier 👤 Lurker #paperwork #DIY #outsourcing
28

Would you rather flip with a friend or go solo?

💡 Example: "I prefer solo - fewer opinions to juggle."

🟢 Low Engagement Barrier 👤 Average #solo #partner #teamwork
29

Would you rather take on a flip with a tight budget or a tight timeline?

💡 Example: "Tight timeline - I can hustle but do not like cutting corners."

🔴 High Engagement Barrier 👤 Frequent #budget #timeline #challenge
30

Would you rather build your brand online or through local networking events?

💡 Example: "Online for me - wider reach with less travel."

🟡 Medium Engagement Barrier 👤 Average #branding #networking #marketing
31

Would you rather deal with unexpected plumbing or electrical issues mid-flip?

💡 Example: "Electrical - at least you can see most of the problems."

🟡 Medium Engagement Barrier 👤 Irregular #plumbing #electrical #repairs
32

Would you rather flip a home near great schools or close to trendy restaurants?

💡 Example: "Great schools - bigger buyer pool for families."

🟡 Medium Engagement Barrier 👤 Average #location #schools #restaurants
33

Would you rather buy a fixer-upper from an estate sale or a foreclosure auction?

💡 Example: "Estate sale - usually less competition."

🟢 Low Engagement Barrier 👤 Lurker #deal sourcing #estate sale #foreclosure
34

Would you rather flip a home with a finished basement or an unfinished attic?

💡 Example: "Finished basement - more usable living space."

🟢 Low Engagement Barrier 👤 Average #basement #attic #value-add
35

Would you rather work with a crew you know or try a new team with better pricing?

💡 Example: "I stick with my crew - trust is everything."

🟡 Medium Engagement Barrier 👤 Frequent #crew #contractors #pricing
36

Would you rather flip a home featured on TV or keep your projects under the radar?

💡 Example: "TV feature - good marketing and fun experience!"

🟡 Medium Engagement Barrier 👤 Top #TV #privacy #exposure
37

Would you rather focus on energy-efficient upgrades or luxury finishes in your flips?

💡 Example: "Energy efficiency - buyers love saving on utilities."

🟡 Medium Engagement Barrier 👤 Average #energy #luxury #upgrades
38

Would you rather flip a home with a challenging floor plan or one with outdated systems?

💡 Example: "Outdated systems - easier to update than changing the floor plan."

🟡 Medium Engagement Barrier 👤 Irregular #layout #systems #challenge
39

Would you rather buy a property you can see in person or purchase sight unseen for a great deal?

💡 Example: "In person every time - too many unknowns otherwise."

🟡 Medium Engagement Barrier 👤 Average #purchase #sight unseen #risk
40

Would you rather flip a home in a bustling city or a quiet small town?

💡 Example: "City - more buyers and higher prices."

🟢 Low Engagement Barrier 👤 Lurker #city #small town #location
41

Would you rather do all the demo work yourself or outsource every bit of it?

💡 Example: "Outsource - I do not need to swing a sledgehammer."

🟢 Low Engagement Barrier 👤 Average #demo #DIY #outsourcing
42

Would you rather flip a home with a massive garage or a sunroom?

💡 Example: "Garage - always a selling point in my area."

🟢 Low Engagement Barrier 👤 Lurker #garage #sunroom #features

How to Use These Templates

To use these templates, simply copy and paste your chosen question into your community platform. Post them as regular content, icebreakers, or conversation starters. Encourage members to explain their choices for richer discussion. Consider using images or polls to make the post even more interactive. Rotate questions regularly to keep engagement high and ensure all member types feel invited to participate.

Best Practices

  • Keep scenarios realistic yet imaginative to spark curiosity.
  • Encourage members to explain their answers for deeper discussion.
  • Avoid controversial or overly complex choices.
  • Rotate topics to cover various flipping stages and experiences.
  • Respond to answers to keep conversations flowing.

All Platforms Tips

For all platforms, use these questions as standalone posts, in Stories, or as poll features when available. Adapt the tone to match your community culture and encourage replies through comments, reactions, or short videos. Tag active members to jumpstart participation and pin a Would You Rather post for weekly engagement boosts.

Frequently Asked Questions

What are Would You Rather posts in a flipping real estate community?

They are fun, hypothetical questions that present two choices related to real estate flipping, encouraging members to share their preferences and reasoning.

How often should I post Would You Rather questions?

Aim for once a week or as an icebreaker during slow engagement periods to keep discussions active and members involved.

How can I encourage more members to respond to these questions?

Prompt members to explain their choices and tag active users for their input. Respond to answers to keep the conversation going.

Are these templates suitable for all experience levels?

Yes, the questions are crafted to be approachable and engaging for both new and seasoned real estate flippers.

Can I edit these templates for my specific audience?

Absolutely. Feel free to customize the scenarios to better match your community's interests or current trends.

Should I use images or polls with these posts?

Adding images or using platform poll features can boost engagement and make the questions more visually appealing.

What should I do if a scenario sparks debate?

Encourage respectful discussion and remind members to focus on learning from each other's perspectives.

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