I have window units in my 4 unit that is in a upper middle class part of Chicago. 

Or pick a point where you keep your day job and stay at a fixed investment level.

If they do, they go to a higher level of care such as a nursing home (higher level of assistance with ADLs) or a Skilled Nursing Facility (called a SNIFF, where medical care is provided).The ALFs I'm working with are all running at 100% capacity and have waiting lists, because there are simply not enough beds.A sharp operator will find an unused municipal building - especially a school - and work with the town building department, code enforcement and fire inspector to get it up to code. 

I was thinking at a portfolio level.

This probably provides an adequate level of protection for Freddie.It’s a concept that is hard to swallow.

My close neighborhood rarely has any fixer upper that fit for a rehab.

@James McGovern, while I don't necessarily agree with your language, I certainly understand where you are coming from.If you truly want to exploit them, then continually report code violations: long grass, broken windows, broken down cars parked on property, anything that will keep racking up the nuisance issues of the property that the landlord not only has to handle with effort but also with money...But, assuming you don't want to go to that level, find the owner and reach out.  

To qualify, property owners must meet specific criteria:Guest stay duration: Rentals must average no more than seven days per guest.Service level: Owners must provide services comparable to a hotel, such as daily cleaning, meals, or transportation.

I am betting that those with the biggest regrets are those that bought at the wrong time expecting COVID level occupancy was normal and those that didn't take the time to learn what it takes to run a successful STR.

You pay them interest, which can be deductible at your rental level.