I am figuring around $25,000. I would hope a GC could handle the whole
mess, and get it all done in a month in the spring/summer/fall.

That will get you far less than half of what you want. If you start in March
it's just possible it might be done by Labor Day, but Thanksgiving Day for
sure. And possibly in the year 2006
The storm doors ought to be only $400 or so, do them first.
Painting the house bright yellow is likely to thrill your neighbors a lot,
especially if there no other rainbow-hued homes nearby. Yellow is a weird color
that people either loathe or merely tolerate.
Waterproofing a fieldstone basement is an execise in futility, unless the house
sits on a gravel hill.
Stay closer to your budget and pour a nice concrete patio instead of the trendy
wood deck. It's cheaper and you can have a fire pit (super trendy) as well as a
hot tub, without killing off 20 acres of ancient forest for your redwood.
I'll defer to other NG experts on pitfalls and possibilities, but for sure you
will have been through some interesting times by the time everything gets done.
Good luck.

Joe