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

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 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.

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).

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

Thankfully I was able to sell both houses and stop the bleeding.During the sale process I found out than one of my houses had a baseball sized whole in the roof and the other had two AC units that were not functioning along with mold that had to be remediated.

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

Midnight leaking roofs, frozen pipes in the street all that.

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.

Milwaukee inventory has just been so low, that even very distressed properties sell to first-time home buyers without a significant discount, so in the end it's cheaper for me to buy properties that already have a new roof, windows, kitchen, HVAC etc