So my thought is to buy a fixer upper to make some quick cash on the side of what I’m already doing.

Clearly, the str has the most to gain/lose and the executive rental is more stable but the upper end is lower. 

It was on it's final legs when we bought the property and we replaced it to sell it.

I would also try to get some part as owner financed, may be even for a year or two because if you assess it as pure business they are trying to sell future revenue potential (pro-forma), but you will be doing the leg work for it. 

Randy - We just bought 2 fixer uppers in the Prescott area and got into the STVR game.

The bathroom is on the lower level and 3 bedrooms on upper level.  

There is a handy search bar in the upper right that makes it easy to find previous discussions, blogs, podcasts, and other resources.

It is a fixer upper, so we are doing some of the work on our own and also contracting out some of the projects such as kitchen remodel, floor replacement, master suite upgrade, etc.

Sounds like you have enough to buy (an FHA fixer upper), and invest elsewhere as well.Welcome to BP. 

Laud for 7 yrs and Sarasota for 7 yrs and I still think Sarasota has legs for flips and Airbnb.