In short: rents and cash flow have not caught up with the rising interest rates since 2022.

Primary Residence is taxed as short-term or long-term capital gains on sale and it may qualify for Sec 121 ExclusionIf you are classified as a Dealer you will pay ordinary income taxes on sale.

Short answer not worth it for this deal. 1.  

Quote from @Collin Hays: I don't manage short-term any more, but can't you include this in a written rental agreement that the guest signs at the time of booking?

What happens if you buy the duplex with a conventional loan with the purpose to build an ADU to move in shortly afterwards?

The short answer to you question is yes. 

STRs in Massanutten - looking to connect w/someone on discussing what a reasonable offer on a STR out here would look like. Also, if you're a serious end buyer and can cover the first part, that would save a step. Not...

Purchase price: $1,100,000 Cash invested: $50,000 Short term rental in Bastrop TX What made you interested in investing in this type of deal?

Quote from @Mike Pepperday: Does anyone know, or have experience with tiny home short term rentals in the western New York area?

With that type of income you can buy rentals with cash in a short amount of time anyways.