This has significantly reduced the cash flow across both portfolios.

For reference I own exactly one handful (5) SFH  rentals in my hometown, all have been purchased in the last 4 years.1) buying at a discount is MY preferred way to reduce risk.

This change has helped generate more bookings, but it comes with a trade-off: guests booking single nights on Fridays or Saturdays might prevent full weekend bookings.Lowered PricesWe’re utilizing PriceLabs for dynamic pricing and have reduced our rates to stay competitive during the off-season.Listed on Furnished FinderWe created a Furnished Finder account to target mid-term stays, which I hoped would solve our slow-season problem.

I'm a small landlord with one tenant (I have two tenants total) in San Bernardino County who stopped paying rent since June 2020, making different claims--work hours reduced and that he's "having difficult times because his coworker died from COVID".

I can’t make someone sell their property, some people will not be reduced to a dollar amount.

Is there any creative way to avoid/reduce capital gains tax on the sale ?

You will likely need to sit on the unit for a long time or reduce initial rent below the market for that unit to rent during the Winter. account for this by either offering a Winter special that will increase to market in the Spring or doing a short lease that ends in the Summer.

A 1031 also adds complexity and timing pressure.Watch Out For:Opportunity Cost: Renovations tie up cash that could go toward other investments or reserves.MTR/STR Management: These models require more time and effort than LTR, even without a property manager.Market Risks: WA properties may appreciate slower than expected, and higher costs could reduce your margins.If cash flow is your priority, option 1 (renovate and STR/MTR) likely offers the highest upside.

A solid pre-screening of the contractor upfront that spells out the expectations should somewhat reduce or eliminate the question of one side bailing out on the other.

Great tenant but property tax increases have reduced my cash flow.