You will have to learn things like the Fair Credit Reporting Act and adverse actions, and there is also fair housing so as to not be guilty of discrimination.

Also, I have been guilty of jamming them myself in past rental units, because it is just so darn fun to see what they can handle!!

Just out of curiosity, have you ever been guilty of PWI (Posting While Intoxicated) in the BiggerPockets forums?

So you can see there are a number of scenarios by which he may be guilty of poor planning or just unexpected costs (which happens a lot with fix and flips), but either way would not be behind in payments or owe money.What I think is odd is that he would need such a small amount.

I feel somewhat guilty about raising the rent and/or forcing the tenants to find a new home , but also anger about my father having been taken advantage of. 

There is no sense in going around and around and arguing and begging and pleading.

Luckily, I run PM on a close friend's property so I have gotten used to saying "I can't say yes or no because I need to discuss further with the owner" and when the answer is "no" to the tenant's request, I feel less guilty in the conversation. 

I know it's a business but I feel so guilty.  

So I don't think I'm quite yet guilty of fill-it-and-forget it. 

And if they did do it, they would feel guilty.