I'm sure you have learned and improved on this along the way.So many people pay too much in advance and get burned.Do you have penalties in your contract for going past deadlines?

But should be the same or similar song and dance. 

As the old song goes . . . you gotta know when to hold em and know when to fold em.

With all of that said, my question is whether it would be wise to forgo buying a property for now and essentially pay my way through school, OR invest part of my savings prior to starting my program, obtain a property, and carry out student loans for tuition and living expenses.

We recommend REIFA to our members and they get a better deal for going through Illinois REIA

Find a lender with a slightly lower rate or willing to forgo points, then take that back to your CU and see if they'll match or beat.Besides DP and closing costs, the CU will probably insist that you have 6 months of reserves set aside.I'm no bridge-loan expert, but my understanding is that these loans are intended to "bridge" the difference between traditional financing and your DP, not finance an entire purchase. 

As for going into commercial, it is really a matter of personal choice: do you want to stick to what you know or prefer to grow/scale. 

There are a lot of different aspects you can bring to a partnership other than money. 15k might be the perfect amount of cash if you were able to contribute by being boots on the ground, meeting with contractors, property managers...As for going at it on your own, I don't know the price of things there but you probably could do some house hacking with that much cash.

What are the laws for going off grid?

The 21st bank agreed to do the loan and decided to do an in-house evaluation and forgo the appraisal.