There are several that I would divest from the start so my total portfolio would be around 22 fairly well maintained homes with maintenance records on the big systems. 

The HOA fees on these now are $1,000 - 1800.

The county stretches from Bailey on the east (50 minutes southwest of Denver) out to Fairplay on the west (45 minutes south of Breckenridge).

Quote from @Andrew Bosco: My latest house hack was a bet on knowing the process.

If you are selling a vacant single family home, I would think a buyer looking to live there would most likely value it more than an investor would, so if your marketing is more focused on attracting investors as an income property, I would also market it/list it as a single family home. 

Most states and some local counties/cities have downpayment assistance programs (DPAs), and a lot of larger lending shops have private DPA programs as well.

Guests are booking on a shorter window of time now, so don’t worry too much about getting rebooked.

One issue I see is when you "buy them out" of the loan, the whole loan will be due per the due on sale clause in the mortgage.

If there's something out there you qualify for, they'll find it.If not, since you plan on using it to generate income you can reach out to DSCR loan folks.

@John Wallace Will you send me information on the house you will be selling?