If you're working full-time, chances are good you're going to need to forge strong broker relationships to help source the best deals.

1)  My quotes for a new asphalt shingle roof range from $4,500 to $5,500.  

It has allowed my savings index to go through the roof while still working a full time job.

(Accouting for vacancy, and repairs bit considering it's a new construction I'd don't think the roof will go out in a year).My dilemma is that I feel the price is on the high side and I also realize I have an appraisal contingency. 

New roof is a definite and I feel theres some issues going on in the basement...

Or is this lack of info worth being concerned about.The inspection is all that matters unless there are warranty items like the roof, HVAC etc.

I painted the entire house and laid out new roof.

My largest electric bill has been $12.00 Roof inspector did not do a great job this time.

Also of course I know it does mean holding back more money for repairs (two of everything, except for roof etc).

We're talking new roof, new electrical (wiring too, not just box), new AC, new kitchen with granite, stainless, porcelain at a diagonal, serious landscaping.