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

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. 

SPECIAL RULES FOR SECTION 1031 LIKE-KIND EXCHANGE TRANSACTIONS, page 135 states:". 01 Taxpayers are provided the relief described in this section if an IRS News Release or other guidance provides relief for acts listed in this revenue procedure (unless the news release or other guidance specifies otherwise)..02(1) The last day of a 45-day identification period set forth in § 1.1031(k)-1(b)(2)(i) of the Income Tax Regulations, the last day of a 180-day exchange period set forth in § 1.1031(k)-1(b)(2)(ii), and the last day of a period set forth in section 4.02(3) through (6) of Rev.

Getting seller to do repairs. 

However, the risk of significant repairs is not to be taken lightly. 

I got a very good price on the building (about $25k per door), but it was a ton of work as in addition to tenant issues, there was TONS of physical distress (foundation repairs, sewer line and water line repairs, electrical upgrades, new roof, and apartment renovations needed for all units). 

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

I've since had to do a service call for the fridge and had to replace the oven recently as the repair was going to be about as much as a newish used one that was in great shape. 

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