I am a virtual broker and we use CRMLS which covers most of the state. 

For example, a $550,000 two-flat in Albany Park might bring in $2,500/month from the rented unit while you live in the other—covering most of your mortgage.3.

Will that be only for one property, or cover multiple properties like umbrella policy?

If the permanent financing will allow you to recover most of your initial investment and the fair market rent covers the principal, interest taxes, and insurance with cash left over, you have a BRRRR.

you said "rent covers mortgage." you need it to be significantly higher than the mortgage to cover all the expenses you are going to incur.hope this helps...

I don’t see where a rental would make sense, so I’m trying to look at other options to cover the monthly payments until the market goes back up.  

There will not be one PM covering all the places you mention in your post, so maybe refine your search a little, and then you can start interviewing.

My LOT was $32,500 and then they added the FOA to cover the first 2-3 years. 

That should cover 2 rental income periods, returning $660 to your pocket.

For the additional features we need that STR apps don't provide, we do the following.esignatures.io for lease signingKeyCheck for background checksOtherwise everything I need is covered by Hostfully, Breezeway, VR Platform, and a few other apps