The reality is we're willing to take a hit through increasing the mortgage (given rates are currently so low) to sort out the roof and painting, so at least we can get the house up to spec and then more easily maintain it at that level. I'd much rather get enjoyment of living in a nice home than doing it up for the next owner!
I was surprised to be told today by one painter that they don't do a layer of undercoat - just prime bare wood then two top coats. Is that the usual current practice? And that still costs $25k??!!