OR a second idea, how about "rent-by-other-means" which I am of course referencing Contract For Deed sale, which is NOT a lease and therefor exempt from rent controls, yet can be written in such a way that operates all but identical to one, I'd argue even better because I can write what ever my heart desires into the terms.

@Dylan DomingueFirst things firstMost 22 unit motels are management intensive as the revenue is too small to afford a top manager or a hotel operator.

That probably doesn't include bad operators, people who paid way too much right before the crash, etc.  

Side Question:I don't want to complicate my primary question with any more variables, but as a secondary, ceteris paribus question.... if the owner lives part time in the STR how does one write off expenses not directly related to STR operation, such as insurance and utilities? 

Curious about this strategy.I have a larger wholesale & flipping operation in Texas.

@Devon Webster - Like others mentioned above you will definitely have more cash flow renting out by the room (check out this company that does it here in Chicago https://bungalow.com/), but it will be 10x the amount of work to keep up with everything, at least until you implement all the systems and processes that would come along with that larger work load.

The proposed ordinance changes by the planning and zoning commission were too strict, and if they were to be adopted I was afraid it would significantly impact our ability to operate as a short term rental.

We have all legal documentation in order including the operating agreement and PPM which was drafted by a licensed attorney. 

I haven't necessarily brought this up with my employer, but I also don't want to get ahead of myself (i.e. take the MLO/Broker License test and then cause issue with my current position).Ultimately, the plan would be to get my MLO/Broker License, and operate my own mortgage brokerage.

He has worked for commercial and multifamily operators that have been hugely successful by raising majority capital from LPs (syndications), but for his personal portfolio he seems to have trouble making that leap.