Most auctions don't care how you pay, but for logistical reasons financing is rarely practical.

If he did a 15-year he could easily beat your $100 minimum, even after adding in the taxes and insurance originally left out.Yes, that would change the logistics (per @Shawn Ackerman) - but will the Seller come at that?

Experience is the only thing that removes fear IMO.I will say,  before my partner/husband, I had always thought about it, and knew it was smart, but feared the logistical part of it as I have no rehab/construction experience... aka paying contractors $$$$  (expenses getting out of control)... so when he came along, knowing he could do all the construction aspect, and I could figure out the financial side, it was a great match and here we are!     

Logistically I'd rather have one payment to handle too.

For all of Amazon's needs to be met I think it needs to be an east coast location and support the growth of Amazon's AWS and Logistics businesses, not it's retail business.

The reason I find this so hypocritical from most of the responses, is I asked a tax and logistics question, and most tried to turn it into a risk of relationship ending question.  

So if you can get higher returns in RE then the logistical thing to do is to keep doing the RE and use the cash flow to pay off your student debt monthly.

Be sure to build that cost in as you use the BP calculators.The next issue you will face is that the logistics of finding a place, looking at it, making a decision, getting it inspected, and doing all the myriad other things involved in actually buying it will be challenging if you are only home to do it for a few days at a stretch.

@Fred Watson have you considered if there’s an additional cost or logistical hassle to do them separately?

" Meaning figure out the logistics or the whole and then break apart the pieces till they get bite size.