Real estate is supplemental for me, not my bread and butter.

Does a 1031 exchange require new debit or can the up leg be purchased with exchange money and supplemented with cash?

My first goal was to get my real estate license to not only supplement my main source of income, but to also become as knowledgeable about investment properties as possible for what I hope to be future endeavors.

There should be some supplemental knowledge there available for you.

Banks also tell me I'd be a bad investment if I were to get a non-legal job in Florida to supplement my income while growing my new firm, since I'd be working far beneath my education level. 

And if you're still working a while you can supplement with savings from real world work. 

The house next door rents for $350 per night and it's just a standard house with no pedigree.With that said, corporate events and weddings would be the big revenue generators supplemented by guided tours when the house was not rented.What I would do is renovate the interior of the house to match the interior of the Brady Bunch TV Show.  

Since you don't have the capital to do the deal without the IRAs to supplement your capital, your IRA is enabling you to make the transaction and personally gaining by the IRA's involvement in the transaction.  

I'm a west coast kid who now has hit midlife and wants to build a few rental properties to supplement retirement.

New, but very committed to investing in rental properties to supplement my normal income.