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

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

Alternatively you may decide not to address the capex but be prepared to deal with high frequency maintenance requests with duct tape 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. 

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). 

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

Deductible expenses include a proportional share of mortgage interest, property taxes, insurance, utilities, and repairs.

You may need to disclose that you repaired this to buyers and want to include more detailed information about what was done.

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.