She proceeded to tell me that her daughter will not be living in the house anymore because she had to withdraw from the university due to “serious medical issues”.

Also, if you don’t mind me asking, how was your success with purchasing at a great price, I’ve attended a few and the numbers get driven up ridiculously My understanding is you can't get reimbursed for just anything, say you go and remodel the kitchen, you'd be out that money if the right of redemption was exercised.

Running the numbers. . . that's the exercise you/we need for everything. 

As for the second time, the tenant had a medical issue which caused her to fall behind. 

If one of your workers (including your friend) get injured on your jobsite you could be liable for their medical costs and disability.

@Juan Carlos CastilloPrivate money is most likely your only option but please exercise caution with these HOAs since there could be assessments in the near future that are fairly substantial. 

The as-is clause allows you to do an inspection and exercise your contingency if you wish, but it assures the seller you are not going to have the inspection and then come to them with a laundry list of requests for them to repair. 

Once that lease is up and it is time to renew, I'd probably have the tenants go on an M2M at that point (as you noted) and then exercise that rent increase. 

I'd exercise any clauses you can in the purchase agreement and get the earnest money back.

For example, how much time do you have to exercise the option?