I don't know how much mental capacity I would have to handle it without it affecting my schooling. 

Currently, I don't have any second mortgages or helocs because the idea of keeping track of more than one mortgage per property has been a tad daunting and decreasing my cash flow at the moment is something I'm battling mentally with.

They have a learn as you go mentality as far as training goes so I feel you need to be a bit more self-motivated starting out as opposed to if you worked for a more well-known brokerage with a more formal training program. 

Kudos to you for trying to work through the current issue, but the S8 "entitlement mentality" is unlikely to get easier to deal with.

Property is versatile posied pretty well for STR’s and long term hold I feel given the location.The investor group seems to be streamlining into new construction and flipping / selling from what I gather (lots of properties on market now and new construction projects in development, I think the selling agent mentioned they had 400+ SFH in portfolio currently they are trying to sell off and transition more so into new construction and large scale apartment complexes) and have own separate businesses in the HVAC / Roofing / flooring world etc.I think my take away here is that I need to get my hands on the previous inspection to see what came up and check it off.

There's definitely a learning curve but as long as you're prepared for it all both mentally and financially, it can be extremely rewarding.Also starting up my first STR here in CA soon... just my ADU we're almost done with at our primary.

And I have already mentally done the gymnastics to be alright with $500/mo. in cashflow.

The tenant is mentally unstable, didn't pay rent over a year, got evicted, forced out by the Sheriff and kept coming back to the property by breaking locks and lock picking.

I think there is a chance that you don't actually hate your rentals, but rather, you hate where your mental health/stress level/amount of free time is.

If he recently lost someone in his family, he may not be in a mental space to process what you need.