Commercial space usually takes longer to rent so you should definitely weight that into your decision.

Lack of proper maintenance2.

I personally would steer clear of Detroit proper but any outlying areas are going to cost you more than $25,000.

If I understand the quantification properly - we're looking at maybe a D+ property in a C neighborhood:The building is from 1925, The roof is leaking in spots, but by no means is it falling down. 

Remember - the rent has to cover EVERYTHING: PITI and management plus your profit after you establish a cash reserve.This sounds to me like a case of what can happen when folks go out and try to do something BEFORE they learn how to do it.I'd look elsewhere unless you're willing to put forth the effort (and likely some "investment") to learn how to do short sales properly.

Hard Money may not likely be a proper avenue for my situation.  

You could reverse the cap rate to find the a proper price.

The AC guy and the tenant feel bad about this situation but I always try to put myself in their shoes and I wouldn't be happy with AC that doesn't work properly.

I attend the bi-weekly Investor MeetUp as often as I can make it.I have a MFH and SFH rental in the area myself, but have not done any proper investment real estate personally.  

But for the first 1 or 2 I think using our own money is the proper strategy.