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

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).

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.

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.

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

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

Had to put a new roof, HVAC, and finish the basement.

Unfortunately, there was a stop work order in place on the property, which the roofing contractor was told by BTC was resolved.  

Also if you know they’re likely to need reservations at certain restaurants I would make a note of that on the menu.

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.