These are top drive-to destinations for much of the Southeast, so short-term rentals here can generate solid cash flow, especially during peak seasons.The area is also seeing steady growth, with more infrastructure and amenities being added to support visitors and new residents.

The peak season is during the summer months, between Memorial Day and Labor Day.

This is especially helpful since your goal is to replace your income and invest full-time.Market Timing: Bend, OR, has seen strong appreciation, but if you believe the market is peaking or stabilizing, now might be a strategic time to cash out.Cons:Losing the Low-Interest Loan: Your 3.1% rate is a huge advantage in today’s environment.

Peak was 2006 and this peak was 2023, so this one was 16.5-17 years.

Framing your position as fair such as explaining the difficulty of finding renters during off-peak months - might help maintain a positive relationship and reduce risks of property damage.Prepare for What’s NextEven if the tenant moves out early, ensure you’re protected.

And, depending on where your properties are in Portland, the value might be near its peak—selling while they’re in top condition could be a smart move.Ultimately, it comes down to what will give you the most peace of mind and the most flexibility for the future.

I guess the only thing giving me hesitation is that it looks like housing prices are at all time highs even after adjusting for inflation:https://fred.stlouisfed.org/se...Housing affordability is worse today than it was at the bubble peak in 2006 if you believe Case Shiller data. 

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

Seems like a good option is STR during peak season and MTR in other times of year.

It never ceases to amaze us how at one for example, we peak at $400/night with solid 5 star reviews.