I hate insulation too and am seriously thankful I only need to do it once. I would not do well installing it all the time.
Your plan sounds like a good bit of work, specially the painting the house bit. I'd rather be building than painting, that's for sure. The new deck will be key though, ours had made all the difference to the house this year.
I plan on trimming out the windows and enclosing the soffits. I hope to just take it a little at a time and I will most likely get to the point where I am going to pay someone to paint. Lol