The market is quite heated now, therefore you must be cautious and have a plan B.

He is great and found a hairline crack in a heating unit that no one else would have found.  

The entire area has been heating up massively over the past few years as all the tech in Seattle is bringing values up in the region.

., replace roof & siding (a few years left in them), 2-zone heat a/c, all new windows (originals still there) and generally take care of the big ticket items now while interest rates are low for the permanent financing, or would you go as cheap as possible to pay down the purchase quicker, while risking getting nickeled and dimed (usually this means out-of-pocket) on repairs for and well as more expensive refinancing in the future?

We certainly don't have the snow but there is some significant heat in the summers!  

All units are on their own power, but use oil for heat.

Siding, windows, roofing, heat systems, exterior, Interior painting, landscaping, parking lot, new appliances, etc. 

I would assume you will have burst pipes from the house not being heated property.  

Heat rises in a home so it "draws" or "sucks" directly at the floor level. 

I painted entire house, new carpet on main floor, original hardwoods upstairs, renovated bathroom, new counter in kitchen, new water heater, AC unit and Gas heat.