His immediate income needs need to be balanced against the longevity risk i.e living for so long that he exhausts his portfolio's ability to provide him comfort. 

If you are talking about apartments that are bigger than an efficiency or a studio, I think tenants expect a kitchen big enough to fit normal size appliances and adequate cabinet space. 

This opportunity would really help me finish nursing school since I have exhausted all of my undergrad aid this semester. 

Very exhausting year, as I have a rigorous W2 sales job.

I have exhausted everything I could think of to improve the process so I’m hoping to find a solution from others.

Always exhaust your conventional financing route before going to commercial or DSCR lending.If you're just beginning, house hacking units is the best. 

*Insert long winded personal story here*, and now I'm 49, chronically ill and exhausted, but finally in a position where, if I can figure it out, I think I could start some real estate investing.

If you research enough you will find that index funds (funds that track whatever market you are investing in like the S&P500, etc) will likely do better than an account with your broker after you factor in his commission.  

David C.owner occupied allows you to get a lower interest rate than an investor loan. 

Definitely look at is as a "process" more than an "auction".