However, my area (high cost-of-living) could make breaking even or positive cash flow difficult.The main question: is house hacking worth it or a "good deal" if cash flow from the rented units doesn't fully cover all expenses but you're significantly reducing living costs?

I will also have another $2600 in pre-paids that cover the mortgage for 6 months and 7k in closing costs.

However you are fined by the govt for not being on Medicare and insurance companies won’t cover you for expenses that Medicare should pay.  

Set aside something each month to cover for it when it does need repair or replacing.Hot water tank: 10-15 yrs max life, $650 if installing yourself, otherwise $800Furnace: also 10-15 yrs max life, $1500-$2000Roof: $7000-$17000+, depending on size and condition.  20-30 yrs max life.  

Will also want to consider putting clauses in place to cover if I sell the building or we end our owner/manager relationship, the lease could come to a end.Thank you

Plenty of homes rent for less than a mortage would be and it wouldn't be hard to cover the rent with some investment in the Midwest.

Obviously, the deal would have to be such we can cover most if not all of the expenses off of the rented units, but if not, could we possibly AirBnB the unit listed as a primary residence to make up the remainder of expenses, or for additional cash flow? 

 $2,595 might not cover everything that you may have to repair or replace.  9 units!  

Especially since this is not in the best neighborhood you are probably looking at higher than expected costs due to turn over.Also if you go down this road charge High Security Deposit cover your back side because you will be using those funds to make ready the unit when they move out in most cases.

I’m renting 1 room out for $950/month, condo is currently cash flow negative by ~$400/month but I don’t mind because a stipulation to my loan (VA Loan) was that I needed to live in it for one year, I’m currently paying $1650 to cover the rest but a 1 bedroom rental in this zip would be upwards of $1,800 + utilities) Currently working 3 jobs and running a small online business to save as much as possible to make my next move.