If we were to rent the whole thing out the initial cashflow would be somewhere between $100-200 month after expenses and saving for maintenance/CapEx.

Maintenance costs can kill your investment. 

As a house-hack, this will not cash flow well -- I’ll need to pay about $350/mo to budget for maintenance and the like, totally doable.

I'm thinking of also asking him to provide building maintenance pro-bono for any small maintenance issue (handyman worthy) that arises on the property and which he is capable and/or qualified of doing.

HOA cuts into cash flow but includes all outside maintenance roof.

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

For example, Our handyman will be on site on Monday May 8, working on the non-urgent maintenance list.

Keep in mind that property taxes are high in Grand Rapids (close to 2%), landlords typically pay for water, and repairs and maintenance costs are higher in Grand Rapids than other areas because you're dealing mainly with properties built in the early 1900s that require a lot of upkeep. 

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Gross annual rents-25% (vacancy, prop mgmt, repairs, maintenance)- annual taxes- insurance= NOI.