Contractor came and I asked him to take his time, if he needs to make holes, measure, knock yourself out. 

I am concerned about make a hole in our roof to vent the fan on my own because I don't want any leaks.

Years ago, a tenant put holes in my walls, and a hole in the ceiling (stomping around in the attic!)

With prices in this area where they are I wouldn't rely on appreciation to carry you out of a hole.

My lawyer said there is activity to try and revoke that law or close the loop hole. 

The next day, 7 or 8 drilled holes, no broken tiles, later, my door is installed, and still working beautifully to this day. 

The roof had major holes in it and what hadn't been consumed by the fire was destroyed by water damage from the fire department.Dealing with the insurance company took roughly 6 months and was a pain, but the house was finally declared a total loss.Depending on how big the damage is, you might want to consider hiring a professional adjuster to deal with the insurance company.

I agree with your last point many people believe you have to be either or and you are either a push over or an a-hole.

If not, I’d recommend taking all the steps to start the purchase process to educate yourself, while understanding that starting 27K in the hole may haunt you later.

Make sure you stock up on plenty of ammunition to be able to shoot holes thru their analysis.