It is difficult to find a broker/agent who really gives a Sxxx and not about the quick buck.

I've run STR/MTR/LTRs and it will be very difficult for you to maintain a solid calendar with only MTRs.But definitely fine-tune your dealings with ABNB....they will ruin you.... 

Permits are very difficult to obtain (we build homes in Chicago, so that may be a non-issue for us considering what we have to deal with here LOL :)4.

Current interest rates are going to make it difficult to reinvest into real estate and not come out of pocket more than $1000 annually, per your current situation.I am also assuming you are paying a property manager with your current figures. 

In my experience, Banks make it really difficult to obtain a mortgage and I have never been able to succeed in obtaining a loan with them for investment purposes simply because they require a certain amount of DTI ratios.

There have been several high-cost damage issues and one where they are at fault and confessed to, resulting in thousands of dollars, that have put me in the hole to the point I won't make anything off of this year's lease.We live in Colorado and it's made it difficult to manage, even with paid professional services, so we are selling as soon as they can vacate.

Also, I think it will be difficult to not have the buyers try to turn me into a custom home builder if they're securing the loan.

The specifics of your and their tax situation would make general advice difficult.

There's so much bad info and just poorly informed opinions on the quality of skip trace services it can be difficult for someone to know what's legit and what isn't.   

As you continue to grow you'll thank yourself later that you prioritized bookkeeping because playing catch up can be difficult and costly.