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I'll second the energy audit, especially a free one, and suggest you pick the brain of every person doing it. Write it all down for later consideration. The energy savings a decade from now will be worth it, if not the comfort level.
This past summer, I got one for $300($100 DTE rebate) and they did a very thorough job, IMO. Well worth it.
-Attached a front door fan which sucked all the air out of the building, and found numerous air leaks around doors and areas I thought were sealed.
-Went though the house with an infrared camera which identified where the insulation was working, and where it wasn't.
-Gave me a video recording and complete write-up of the previous, followed up and later helped with the rebate forms, and recommended possible fixes.
I suggest the energy audit first because it's no use spending $10,000 on windows when the wall insualtion could be bad, a ventilation system needs improving, or another factor is affecting the home.
Even a hundred dollars of caulk might make more of an improvement.
On the drafty doors, we simply added curtains. They stop the draft in the winter, and the sunlight in the summer.
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