These tenants will make their next move into an assisted living, some are very price sensitive, under market rent, and/or not really and truly able to fully care for themselves or their spaces and we generally try to gently nudge these tenants into more 'assisted' living situations be it with family or professionals.

So if they update their ordinance, or request I simply continue to pay the double fee even if they don't, no skin off my teeth.

It was like pulling teeth half the time.

Getting 5 star reviews is a learning curve as you need to be a good communicator and be sensitive to guest needs, staying booked is about demand and whether your place is priced appropriately.

Especially if you're very cost sensitive. 

The conviction would still pop up for more sensitive employment searches like police officers or day care workers, but it wouldn't be reported on this sort of a background check.

Unfortunately the lot we may buy is from family members and therefore time sensitive and price is fixed.

For example, I know some landlords are more price sensitive, while others care a lot about quality and customer service or even Google reviews.

Understandably a sensitive subject, but ultimately you simply want to protect as much of your Father's assets as possible (again, I see your point that even if you're not paying capital gains from your own pocket when/if you sell- at least avoid how much is paid from funds that were inherited from him in time, protecting what he worked to acquire over the years- not money hungry, bottom line smart).

Doable and easy are two very different things and I firmly believe that most people getting started are best off, even in an expensive market, doing some kind of a small multi-unit live in rental to cut their teeth.