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. 

Check your roof.  

Fix Flip- only do surface style changes- flooring, landscape, roof, windows, etc. 

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.  

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). 

Quote from @Brian Cerezo: I’m in search of a roofer that can patch up my roof in my rental in Canton Ohio so I can get it ready to sell.

It's very simple, here is the header for one sheet:# Of RentalsAddressDate BoughtYear Roof was put onCost of PropertyValue of Property 2017Value of Property 2021TaxInsuranceMortgageMaint/HOAAC FiltersRent Per MonthThen I have another sheet to keep track of any expenses for the year:# Of RentalsAddressCityJanFebMarAprMayEverything is very organized on these two sheets for the CPA every January.

Luckily I had war fund saved up for the HVACs, roofs and foundation repairs I needed.

If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

A kitchen fire in the back unit got a little out of control and burned up to the roof.