$200,000 used to feel like a powerhouse investing budget… but in today’s short-term rental landscape, it doesn’t go nearly as far as it used to.

In this solo episode, Kenny Bedwell breaks down the hard truth: $200K is the new $100K.

Competitive STR markets have leveled up, amenities have escalated, and investor expectations have shifted. Kenny walks through why $200K no longer guarantees entry into the big-boy markets (Smokies, Bradenton, Asheville, Bourbon Trail), what buyers consistently misunderstand about down payments vs. true budget, and how to think like a strategic investor rather than a pre-approval chaser.

He also unpacks the 20% Rule, the reality of amenity wars, why your biggest moat is future thinking, and the path newer investors should take when they have less than $200K to deploy.

If you want to make your money actually work and stop getting crushed by competition, this episode is your roadmap.

Timestamped Highlights

[00:00] Why $200K doesn’t stretch like it used to

[00:01:20] The psychological trap of buying based on pre-approval

[00:02:10] The 20% Rule: what your true budget actually is

[00:03:20] Why a $500K home can require $200K to do it right

[00:04:40] Competitive markets and the real cost of keeping up

[00:06:00] When big brokerage agents start pushing a market… it’s already too late

[00:07:20] Why chasing what worked last year won’t work now

[00:08:10] Downsizing: why a killer 2–3 bedroom beats an underfunded 6-bedroom

[00:09:20] The amenity war: pickleball courts, splash pads, heated pools, full design

[00:10:50] Real estate finance lesson: why abnormal returns disappear

[00:11:40] Today ≠ 2021: why $200K no longer buys performance

[00:12:25] How to pick markets with lower barriers of entry

[00:13:10] What “drivable markets” really are and why they outperform

[00:14:35] How to read metropolitan travel patterns for hidden gems

[00:15:40] Why most investors are psychologically wired to overleverage

[00:16:20] The only way to compete with bigger players

[00:17:50] Planning for future competition, not past comps

[00:18:30] Kenny’s Walkins Glen example: $350K → $144K gross

[00:19:30] Why futuristic thinking builds moats

[00:20:10] The Autopilot app story (Nancy Pelosi portfolio tracking)

[00:22:15] Understanding how investor flood-ins flatten returns

[00:23:20] How to pick properties that will hold up against new competition

[00:24:30] If you want a moat, you must create it

[00:25:10] Kenny’s offer to break down “moat categories” in a future episode

[00:25:50] How to message Kenny directly with questions

Mentioned Resources

• Autopilot App (stock trading tool tracking politician trades)

Important Links

• Want us to find the deals for you? https://strinsights.com 
• Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df 
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.