I am the Chairman of the Wicosnin Real Estate Investors (formerly WAA) we do the lobbying on behalf of the Wisconsin landlords at the state level. 

I would speak with a loan officer to get an idea of what I would qualify for with that level of student debt. 

Which is why you need the advice and counsel of an experienced, and skilled pro - everyone with a law degree will not provide the same level of advice. 

That level of being locked in like that, that's been the number 1 indicator I have seen working with all the people I previously mentioned of who is gonna make it, and who's gonna flame out.

if not they may not know the high level details of the asset class that make a difference when buying.Dollar stores the Dollar Generals are currently BBB- investment grade tenants so can get better loan terms with lenders.

You will want to have properties under contract before bringing a contractor out to walk the place with you.If I were in your shoes I'd have a 30 minute call/zoom/coffee with a couple of local GC's now and come prepared to explain to them exactly what you are looking to do.For example when I first got started I was targeting single level, 3 bedroom, 2 bathroom, 1,800 square foot homes, with 2 car garages, that were sitting on 7,500 square foot lots, and that were built of block in the 1950s/1960s.

Imagine a 4bed/2bath home with a small ADU in back, a converted garage with a private entrance, or a three-level home with a basement that can be converted into a private apartment.You can get privacy and house hack, but it takes a little more effort.

As long as its rational and both parties are level headed im sure you will figure it out. 

No, but it depends on your comfort level.

The 2-story building had a restaurant on street level and office spaces on the 2nd floor.