Obviously this is a very generic question and property specific so I'm just looking for general thoughts from folks involved in the area.

I've been working with her...I know, probably a mistake (sigh)…but I'm in a soft rental market and she does at least get the full rent paid (plus late fees), albeit in pieces.As an aside, wWe had a "Come to Jesus" talk and supposedly she is looking for a p/t job to supplement her expenses. 

There is also a supplement homestead exemption for 25-35% depending on the home value.  

Not in your area, but with that much work, I would reach out to 3 local vendors  with the sizes of each house (in square feet), where the air handler is located (attic, closet, garage) and ask them to give you a quote on a package deal to replace them all with whatever brand of unit you prefer (like Rheem, or if you are ok with a generic to save money).  

How many deals have they bought.It seems every time I run across these guys (not the two I mentioned specifically, I mean 'these guys' in a generic sense) it's always some group of people who are trying to pool money together or use OPM to make a deal happen.While how many properties, or the value of your RE isn't a pissing contest, I would want to know that before I gave someone $10k to "mentor" me.  

Did you partner with a GC to supplement for lack of previous GUC experience or were they willing to sign a guarantee?

However, I got into real estate investing as a mean to supplement my income to pay for school and get out of debt.

Yeah you deserve to struggle (the generic you, not you, you).While you and everyone else is obsessing with Google updates...

Essentially CA supplements your property taxes.

This is straight cashflow of course which is nice, but you want to roll this into more cashflowing real estate assets, not leases.This business model supplements my buy and hold rental portfolio nicely.