You will be taking some risk, but there will be reward.

He's now a top producer, gets his entire cap BACK as a reward, and has a local team of a dozen agents.

I've read numerous books and rarely have come across any information relating to section 8 housing (and even those snippets haven't been terribly helpful or accurate).

Depending on your needs Index Universal Life may be more rewarding that Whole Life, but both are complex products that can be very powerful in increasing your yield if used properly. 

Certainly don't give up... but maybe change your criteria and keep an eye out for something a little bit more safe for your first house-hack because having a stable foundation in a real estate portfolio is the real path to success in investment... risky purchases with big rewards might seem like a good way to start investing... but unless you have a lot of experience and cash in the bank, its just glorified gambling in my opinion.  

It's very fun and rewarding, both personally and financially.

The reasons for financial problems are numerous and varied.

Unfortunately, we have had to apply this across the board even if tenants have been late numerous times in the past. 

I'm in the process of closing on the MA property and I think it will be both a good investment and a rewarding experience based on my conversations with Property Managers and also because I have a great deal of family in that area. 

In terms of Ybor, that is a HISTORIC neighborhood all by itself so while it is a risk, I can see great reward if the neighborhood turns around.