The government has tried it with section 8 and rent control in some cities , we all know the end result .You would be better off starting a jobs program teaching the trades , educating them on finances and work ethic and then rebuilding abandoned properties for them to buy 

For 10 years, every arriving party in my STR finds 1) a fresh bowl of fruit, 2) a local city magazine and a weekly periodical and 3) 2 bottles of wine (1 white, 1 red, 1st bottle is complimentary, envelope to pay for 2nd bottle).No great expense, but "wows" the guests every time. 

You can do some really cool, unique, and creative designs with containers.Do seniors want to build/buy in a rural area vs city area? 

In some very attractive markets like coastal cities I can see it being worth it not to rent the unit or rent it only under very limited circumstances in the low season because the high season is just too lucrative to allow anything to affect those bookings.

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

What city are your properties with them in?

The City of Montgomery is the Capital of Alabama with a robust economic environment that has produced multiple awards of excellence at the Chamber of Commerce level.

Most of the tax experts who specialize in real estate work completely virtually these days.That said, a local CPA probably does have an edge if your state has state income tax and especially if your city has a local tax on top of it.

There are still liens today leftover fro the 2016 Baltimore City tax sale.

No off-street parking = not worth doing MTR unless it meets all of the following: super urban area where no parking is the norm, highly desirable area with a ton of MTR demand, super safe part of the city, and has great public transportation (think NYC, Hoboken NJ, etc.)Unless it meets all of the criteria above, I pass on those opportunities because my MTR will be eliminating the many people that travel with their vehicles.