I'm still completely new to this but aiming to purchase a property this year.

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

On a side note, The House Ways and Mean Committee has released text on a bill aimed at exempting certain balances in IRA from RMDs. 

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

Your customer is different, are you aiming at future homeowners or other investors?

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.

In your opinion, would you say that an investor should aim to buy below market value or can you still cash flow paying retail?

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. 

There is a meetup called “AIM”, I believe, for Apartment Investor Mastery.