Keep it up and adjust your systems to get better and better with each transaction!  

Being built in the 1890's means that ALL systems in the home have surpassed a useful lifespan and it's not uncommon to see some of these historic homes still hanging onto their "firsts", especially in windows, gas lines, HVAC ducting (which would have been added much later than the original construction date), etc. 

@Michael FriasI have actually done this not in Detroit specifically, but 35+ wholesales without ever seeing the property, it was while working for a real estate investing company, under an experienced investor who had more than 10 years experience investing, 10-15 VA's that I managed, and a bunch of systems that made this possible... even still it's not the best way to do wholesaling at all, and it wasn't my desired route but it worked at the time.The specifics as to why it won't work:You need to be experienced to wholesale properly.

Does this system make sense? 

The thing I don't like about the tri-state area is the anti-landlord legal system.

The best approach is to hire a full time onsite management team that is experienced, and capable of performing all the duties of management, home sales, managing maintenance and repairs, and the implementation of software systems and processes that will eventually have the park running like a Swiss watch.

A $3,000 A/C system replacement would generally be a restoration relating to the HVAC subsystem of the building and thus capitalized, not expensed. 

Like others are suggesting here, it’s really really really valuable to meet other like minded people.(2) build a system to find leads (search FSBO on Craigslist, drive for dollars twice a week, etc) (3) don’t be afraid to walk away from a deal if the numbers don’t work or if the margins are thin (there is ALWAYS another deal to be had, think abundance!)

And your description makes me think that you do not have a bookkeeping system in place.

Seperating the meters legally would easily cost more than a new roof or HVAC system would ever cost.