However, for me, I would rather just pay someone and not bother with finding tenants, dealing with repairs, etc. 

If a landlord needs to enter a property for an inspection or repair, a two-day notice is required.

For me personally I am not handy when it comes to repairs and such.

.- Learn how to do your own repairs & rehabs to save money now.

Once, a tenant left a massive stain on the rug beyond repair.

The partner will help with holdingf costs, closing costs, repairs and get half of the equity.

I am just looking for insight from local MA realtors, attorneys or landlords regarding what my typical monthly expenses (if any) will likely be (I don’t mean one-off expenses like roof repairs). 

I have just over $200K left of owner-financing, but I'd like to obtain a cash-out mortgage/loan of $500K (ideally) to be able to pay off the previous owner and make some repairs, etc. 

Consider FHA loans for lower down payments and reserve for repairs or upgrades.

They're fine for buying a turnkey, older home that gets "spruced up" and comes with a 1-year warranty on their repairs.