Love my food. 

No to very little crime no worries with water or food borne illness's  etc etc.  

For example, Yunta in South End is a must-try Peruvian spot with amazing food and a great atmosphere.

We have our Guide Book on the counter in the kitchen.People like to have something to look through, plus other guests leave flyers from places where they ate etc. with notes like, "Great food" etc. written on them. 

Two weeks later I stopped by the unit (was passing by and decided to take a look) and found that someone was using the shower and leaving food and clothes in the house with visible intent to return.

I’ve been self-managing a single-family rental (SFR) for a while now, and I’m interested in taking my property management skills to the next level.

You could lease part for food service or coffee shop and some retail space, a small health club, massage. 

I know that a ton of people will win with the approach you are contemplating taking - in taking a HELOC out for the down payment on an investment property. 

You are twice as likely to die in a bike accident, 4x as likely to choke on food, and about 90x more likely to die in a car accident.

I have no idea on how any of that works, but if he is serious about getting into RE and if that's what he wants to do....then do it. 1500/month is about minimum wage, I don't see that much risk in taking the leap into wholesaling if that is what he stands to "lose"