The worst experience we've had was with a flat roofer (very common roof type in Chicago) we finally wrapped up, after waiting almost two years for them to finish/fix something. 

What's the life expectancy of the roof, paint, furnaces, water heaters, etc.?

Or just avoid ST booking platforms.2) Converting the roof into a terrace (apt. on the top floor).

Details on the duplex:Price: $385kBuilt: 2012Size: 2674 sq ft (1333 each side). 2 story, 3B/2.5B each side w/ 1 car garage & driveway for both, fenced backyard both sides.Interest: 5.49%PITI: $2,698Current Rent: $1,350 but could be brought up to ~$1,600, maybe $1,700Yearly Property Tax: $8,340 (I don't pay any on my side while I live there so $4,170)Upgrades: Vinyl floor in kitchen of both units, new AC (central HVAC) on vacant unit, roof done 2016. 

after seeing all the risk management/insurance that comes with tenants wood fire usability, I was wondering the same, or, actually:   I'm thinking to seal the cap on roof and run a cord putting an electric Infrared heater fireplace in there, so they can still open the glass and get heat and watch TV over the mantle, but can't burn anything or have any flame.  

The need for a home and an office under one roof.

With experience spanning nearly every aspect of real estate—except direct title work—I’ve had the opportunity to work closely with many talented vendors in the Indianapolis area.Today, I’m on the vendor side at Trojan Roofing Company, where I continue to serve the local community.

Check your roof.  

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). 

The excitement then went through the roof and the owner wanted to do three or four at the same time and the next thing you know the whole ship went down in bankrupt.Just something to think about.