If you're not sure of you preferred direction with your next property I would invest in understanding investing more thoroughly and read 5-10 books as well as speak to other experienced investors.

I often read that one should seek a commissioned sales role because your comp is uncapped and that has served me well. 

After punching your rental income from tax returns MOST people more or less break even ion a rental.

I learned a lot about managing an STR, specifically with revenue management and guest messaging.

I say "may" because while I have read about this in several places, I have not personally verified this to be true.I usually pay contractors by check the minute the work is finished and approved.  

I have 2 properties now one I live in but Short Term Rent it when not home which is a lot.

A lot of those new construction projects in Bronzeville are on a slab and framed, as I mentioned above!

You will be taxed on way more than $150k, and also this $150k number is totally irrelevant for the tax calculation anyway.

The park will be a lot more tricky to finance 

Unless the borrower is self employed and takes a lot of expenses to show lower income on their returns then it usually makes sense to pay a couple thousand a year in higher interest (you can pay like 4,000 a year in additional interest for DSCR if you are saving 30+k on your tax bill kind of math lol)