If the covenant specifically prohibits renting out rooms or STRs, you may be restricted from doing so.You should carefully review the covenants tied to your property to understand the specific restrictions.

I've always worked for myself and didn't have a ton of support so I was not able to prove my income for quite some time due to doing my taxes wrong or not understanding how things work.

Search 'STR arbitrage' on this forum to get an understanding of what it entails.

My due diligence process was certainly tightened up after that deal and analyzing properties and understanding what things will cost is now 2nd nature to me. 

When we did it, we did score some great deals, but what we found was that we were visiting so many properties to understand our "strike price" (the maximimum we would pay for the property when taking into account rehab costs, hold times, interest on any debt, closing costs, real estate commissions, a contingency reserve for "unexpecteds", etc) that the math started to not make as much sense.

If you are single or married without kids and an understanding spouse.

Understand your niche!

I don't recommend it unless you can find a CPA who really understands the syndication space. 

I was told I need to get a good understanding of these subjects:  1) Taxes, 2) Legal issues in ABNB, 3) Negotiations, 4) Short Term Rentals & 5) Tenant/Rental Agreements.

I understand the 25k guy .. and the seller carry back folks normally those I see that do that will get the amount they paid for the dirt back in the down payment and the note is pure profit.