And it could take even longer than 6-12 months to find a replacement depending on the area.The other things to look at carefully are major Capex or maintenance expenses - you didn't mention whether this was a NNN lease.

The majority will most likely want an equity position in the deal, and since wouldn't have an active role I'd be getting into a syndication rather than just a JV.

Purchase price $525K, appraised for $760k (no major nor significant Reno was had). 

Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

David, this deal could work, but I’d want to dig into a few things first. 80% occupancy with long-term tenants is solid, but what happens if a major tenant leaves?

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

I'm reaching deep into my psychic thoughts… I see it… A majority of people who respond to this post will be real estate brokers… I can see it!

the majority of even my national users are looking to keep cash in reserve and as such are looking to landlords to finance that TIA as additional rent at a return premium and then that extra rent bakes off in whatever term is negotiated. 

Hot tubs can be a major revenue booster for STRs, especially in colder climates or vacation destinations.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.