They will place them with minimal screening and they cause lots of maintenance issues and do not pay rent in time.

I think you need at least $10,000 in reserves, or bare minimum at least enough to cover a month and a half of rent, utilities, and any unforeseen maintenance issues per property.

What's the issue with taking losses on a Single Family Home? 

An if they don't meet that or whatever other guidelines you put in place up front, then there should not be any issue denying applications, and maybe they don't even apply.Personally I would not make up conditions as you go.....have to treat everyone fairly.

Major concerts, Broadway and symphony performances, extensive permanent collections and traveling exhibitions contribute to a wonderful way of life.

Timing of the sale of each might be an issue, it's a complicated strategy you will want to think through and plan for before you list either property. 

Basically covers what most of us already know about these major metro areas.https://www.dwell.com/article/rules-for-short-term-rentals-a...Worth a read to see how those regs came about.

A way I came up with is my family owns a small restaurant and a majority of our clientele are older people.

Reasonable priced major city but looking at other cities now potentially but haven’t invested the time into understanding another market yet.  

We must send you a letter before issuing a fine.