I am based in Houston and currently embarking on my journey into the world of real estate wholesaling.

You are correct; it would be awkward having two different parties staying on the property. 

Basically, more than a certain amount of STR and MTR in the same building were considered a hotel and I would have had to have 24/7 staff on site.Were you able to get around that with the local municipality?

Focus on LocationChicago’s rental market varies widely by neighborhood.

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

At this point, I'm not so concerned about achieving that exactly, but if my REI journey takes me there on my way to (or even after) financial freedom, then I'm all for it.There's still some work to do to prepare financially for "the first deal" and that moment legitimately appears to be about 2 years away. 

If you can find an investment that pays for itself, you won't be so nervous about investing.I also recommend you educate yourself on how to manage well.

I don't know how the really big players stomach it.Something else I failed to mention was how the PM's are also tacking on fees on top of rent to extract even more money from our tenants. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Additionally, while rates aren't historically bad right now, they are higher than 4-5 years ago, and they will be even higher for you as an investor than they were as an owner occupant, which is what you were when you bought originally.I get that you are anxious to add to your portfolio, but that could be achieved without touching your first golden goose.Sometimes on BP, the push is to leverage every last spare penny, but that can be a risky game as the markets shift.