Do they have a small child.

Although I like the thinking, not something I'd be comfortable with or recommending to anyone I know.  

So when deciding a PM company to use, you are the one to decide what you are most comfortable with and what you are not.

The plus for him doing something like this is that he is in essence buying a real estate backed note and backed by a piece of real estate he knows and is comfortable owning.  

I would recommend getting comfortable on the phone and working with sellers before trying to add techniques.

@Justin Godlewski Yes, get comfortable disappointing the list price; one cannot loose money on a deal to be successful.Ignore the list price and offer what you think it is worth, this takes practice.  

Our place really looks nice and we can make it very comfortable/high end for guests.

If you can get a 10-15% return on this equity then I think it makes sense.You'll just want to run the numbers and see if you're comfortable having a higher mortgage payment or paying off that line of credit.

In the meantime one big lesson I have learned is not to jump into anything until I feel comfortable and smart enough not go get hurt.

I treat people really well, laid back, comfortable, etc.You can spend time and $ with all that other stuff they teach you in classes or just step out and do it!