I had originally planned to source the down-payment through private money of someone I know but it doesn't seem to be happening right now.

Wholesaling isn't necessarily something I want to do but I'm studying all aspects and avenues of RE and it is fascinating how contentious this one issue is.Back to my point:  Again I think this site is an invaluable source of information but, when I comes to Wholesaling, the folks at Bigger Pockets seem to be almost unanimously for it as a legit way of making money. 

Considering I have free food and shelter, should I just focus on studying real estate and making money to invest or should I attend college (approx. 4k a semester)? 

Your ability to put money in or required credit will vary source by source.

Biggest individual expense being food as I have a special diet due to my Chron's and Celiac.Everything left over goes towards paying down debt.

Elance & oDesk are being acquired/rebranded by Upwork...Upwork  also has a recruiting team that can help you find a great freelancer based on your job specifications, budget, required skills, etc.The recruiter will source and invite freelancers who fit the requirements to apply to the job and shortlist the best applicants for you to interview and hire.

You just have to pay for your own drinks and food.  

So the underwriter looks to see where you are now with ALL sources of income and debt vs where you'll be after the purchase  and applies their maximums appropriately.The brokers I have worked with would not allow the 43% DTI as in your scenario, @Justin R.So the key is to either buy a rental such that it does not send you over the maximums or reduce your other debt or increase your other income until the ratios work.  

On a recent short sale we did, there we had to sign a form certifying that the seller would not continue to occupy the property through a lease or otherwise..What is the source of this prohibition and why?  

I feel that they won't have problem paying the rent, but with utilities and all, plus food, etc..