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.

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.

It's going to need a new roof here in a few years, and new flooring in both units. 

I’m on the verge of giving Booking.com the boot , too many cancellations and the worst part is when you call customer service, which is China ….in order to validate you as a host they give you a call back so you can’t get your answer quickly and the callback takes a few minutes and half the time the call does not make it through- enough to make you wanna scream.

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

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