I have a plan in place to buy a 4-plex and live in one of the units for a year and also negotiate closing costs to minimalize my out of pocket investment.

I have a plan in place to buy a 4-plex and live in one of the units for a year and also negotiate closing costs to minimalize my out of pocket investment.

We would also self manage this but would hire the work out to turn over the units instead of DIY to minimize vacancy. 

If it is minimal, no issues.

It would minimize your losses through commissions if they would exercise the option part Most likely still end up losing money each month.

If you're trying to make a minimal down payment it's not likely you'll see positive cash flow but the rental income will offset some of your living expenses.

Minimize all living expenses.  

Given that there have already been a few surprises with this property and I'm not sure how confident I can be at this point that the deal will progress to closing, what's the best way to minimize both mine and the Seller's out of pocket exposure in the event the deal falls through quickly?

I have closed on a few properties a long time ago and it really wasn't that difficult from what I recall and I had zero experience at the time and zero issues as well.However, now I would suggest calling a local real estate attorney and ask about their services to write the contract and perform the closing for you.It could save you some big money with the realtor commission and besides you are getting valid legal advice and minimizing your legal risks .

-student loans are a racket. if you can afford to go with minimal debt then it may be a good investment for you. if you have to take out a lot of loans i would suggest get a degree in something that translates into a good job, something like accounting, hard sciences, that way you will have a good shot of being able to pay off said loans soon after graduationConsidering your position with your mentor.