You must have your personal finances in order before you invest.

Offered to intern/work for him at half the pay as his personal assistant if he would teach me everything he knew.

This is the foundation of why LaPlante Real Estate is based in portfolio management and property management... my personal portfolio started in 2009 and I find the majority tends to be Section 8. 

Would even be happy to meet in person since we are in the same area.

A realtor doing high volume, you don't have to use one you can poll 3-5 agents see what they do to get you the comps and then pick that person to help you.

While personal circumstances can vary, it will be a unique situation indeed if $10K in debt should force you to declare bankruptcy. 

Do you own a personal residence yet?

I don't have personal experience with it, but when the app was first developed, I contacted the developer and put the app through a fairly robust test usage to see if it's something I would want to recommend to my clients (I'm a CPA).I think the app is great for its intended purpose and I do recommend it to my clients now (and have for about 18 months now). 

There are many resources for you to connect online and in person.

If you see work crews reaching out, ask the person in charge of securing housing where they go looking.