Quote from @Carl Rowles: Aside from the stigma of them, it seems like they’d be a decent entry point for new home owners, given the housing market the way it is.  

Found it on Facebook marketplace through our wholesaler that had gotten the deal from the previous owner before he had passed away so purchased it as a probate sale so I was able to get it far below market value.

So the actual tax bill is going to be impossible to predict without looking at the individual owners' personal tax situation.How much of a gain do you think you made on your first flip?

You aren’t owners with lease options.

I had a similar off-season challenge and decided to allow pets ( with restrictions and clear house rules) and I gave a 30% discount to try & attract  snowbirds ( I’m in FL) - my calendar filled up for a few  months with a few pet owner bookings and  2 separate 45 night bookings,  did all this on pricelabs & airbnb -best of luck ! 

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

Think lakefront properties in small towns, destinations with new attractions (casinos, amusement parks)...Another idea is investing in properties suitable for accessory dwelling units to create dual-income setups, especially in cities with relaxed ADU regulations.

I advertise the houses that way, even if there's an appliance or two that the previous owner has left in them and I don't mention them so that the people coming aren't (or shouldn't be) expecting to find them. 

Yes, it is possible to obtain a second FHA loan, but only under specific circumstances, as FHA loans are designed primarily for owner-occupied properties.

Rules/policies are subject to change and selling units in some buildings can be challenging.Condos, on the other hand, typically have more lenient rules/policies oftentimes allowing for unit owners to rent their apartments immediately and indefinitely.The rule flexibility, however, comes with a price.