I have nothing to say about the siding, but we have had several quotes on AC for our house and they have almost all made me want to vomit. When we first moved here we got a quote before moving in because I really wanted air conditioning, and it was $8,000 which didn't seem too horrible. But then we moved in and really thought about it and his proposal just didn't seem like it would really adequately cool the house. So we have had a few more and they have all been in the $15 and up ball park. And aside from swallowing the cost, I would have ducts in my closets, which are big but laid out funny so we never have gotten around to doing it. A minisplit won't work so well for us because there's not really a good place to put one, we have so many windows.
Last summer we broke down and got air conditioners for the windows in the bedrooms - we had a new baby and new babies like to sleep swaddled but I couldn't swaddle him on a 90 degree night without fear of cooking his brain. So now we can sleep comfortably in the summer at least. We have a finished basement so we hang out down there a lot when the weather is hot, it's like free air conditioning.
The funny thing is we recently made and walked on an offer for a house that had forced air heating and cooling - and I couldn't get excited over it, I just felt it would be WEIRD to have AC. The girls room would have been the attic so we would have had to cool their area (there was a wall unit up there, rest of the house was central) - the basement was unfinishable, we would have lost our "free" AC. So weird that I have gone from wishing we had AC to feeling like it would be weird to have it!
Even our first floor doesn't get TOO bad during the day in the summer, I guess they planned for such things back then. It's the upstairs that can be bad. So, we will just get by with window units.
As a bonus, the units we bought have this water recycling system so when the unit cycles on, it makes a very pleasant gurgling sound... it's really enjoyable to listen to at night. Sometimes I wake up at night and wait to hear the AC gurgle before I go back to sleep.
So strange the things you come to love about old houses...
1938 or '39 craftsman-like bungalow-like kinda thing