Then you have the chance your local bldg codes will require upper floor egress sizing (triggered simply by the window replacements). 

I've got a home warranty for a year from the seller, but I'm aware that I'm going to have to replace a couple of big pieces within the next few years as the house is now 20 years old.  

My tenant broke the bathroom faucet (high-end Kohler) 4 months into the lease.  Is this considered outside the realm of wear and tear?  Minor repairs are the tenants responsibility but I want control over what is inst...

Sometimes, in the long run,  it's cheaper to replace something, rather than fixing it. 

Gets back her money in about 2 years on the replacement trailer.

Just put a regular old roof on, and replace it every 15-30 years depending on how it holds up.  

It is still not perfect and you will replace and tweak as you go still. 

In my area many old school buildings are being replaced with new schools, contractors and investors are buying up these old schools and turning them into residential apartments and commercial spaces.

The house is not at all live-able, between the mold and just the overall poor conditions of the interior and the roof needs to be replaced, so I think right now we are moving towards not buying it, rather than buy it and sit on it.

~My top is AC, I have already decided I'm replacing the entire unit next time I have a problem.