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

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

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.

Some can charge less on a job and some charge more on a job. 

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.  

On this one, literally sitting there with the seller, in the property, it was a lot to take in.

Have you run to ground all the more common issues?

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.

A lot of real estate contracts include due diligence periods for exactly this reason.If there are no contingencies, you could still try negotiating with the seller.