Both houses need a new roof that will cost 15k. 

Amortize your major repairs (roof, hvac, built in appliances) and add an estimate for small maintenance.This feels not terrible to me.

I then hired contractors for plumbing, electrical, roofing, and HVAC upgrades.

I then hired contractors for plumbing, electrical, roofing, and HVAC upgrades.

I would at least recommend you have them shop a policy for you.One thing we did note is that with hail damage to roofs, they seem to be decreasing coverage/increasing deductibles on that if ever needed.

Once the interior was stripped and the infrastructure tested, I brought in commercial contractors to handle critical systems like plumbing, electrical, roofing, and HVAC installation.The house, built in the early 1900s, was originally a coal-burning residence.

Double check any cap ex you might have coming in the next year or more there so you can plan to set that aside (boilers, roofs, etc).

And I may get multiple bids for the same work, like multiple paint bids, multiple roof bids, multiple flooring bids, etc.

Guy who inspected gave some report asking to fix the issue on roof and if it’s not addressed they will terminate policy by January,15th.

i don't recommend buying a random property in a random midwest state for $118K that looks great but actually needs a new furnace, a new roof and a new sewer line, and will crush you with capex and make you sad.hope that helps.