are there specific geographic regions you're sticking to? 

I look forward to learning more about what specifically you are looking to do 

This is where I have a lot of House Hackers go wrong, as they are just focused on the cashflow aspect. 

The data collection websites like awning, can be unreliable and don't factor in the specific amenities/upsells that a specific rental has. 

You're in a good position and there's nothing wrong with the strategy you described.

I could be wrong on this but I seem to remember reading about this in one of my CRE class's for my CA Brokers license.

There might be software or agents that can help that more specific to your area you’re looking to invest in. 

REP status is specifically trying to override this $150k limit, but it's out of your reach, unless you have a spouse who can qualify.Rules for STRs (short-term rentals) are different and do not require REPS. 

In a state that a lender can get a deficiancy judgement if the deal goes through foreclosure the client can get their credit trashed and end up with a big fat judgement against them.. ( state specific).the reason your probably getting buyers that want to do this is because of all the online notoriety currently like Pace Morby who is huge in the space and the legions of students and followers and then to a lesser extent there is BP's own Sub to Guys..

Did some reading on your bio - Noticed you were interested in investing in commercial real estate, what draws you to that specifically?