As a generalization, the older the house is, the more issues you will have. Technology has changed a great deal in the past 15 years and houses built today are vastly different than ones built in the past. One reason is that the enforcement of building codes is a recent development up here. Old houses obviously work because they are still standing and functional, but the mystery of the unknown is something that can wear on some people.
As houses age, they can start to degrade. Mechanicals break down, unprotected wood starts to rot, shingles start to curl and leak and the style becomes outdated. At a certain point the decision will have to be made whether to remodel an older home or to tear it down and start for scratch. The newer the home, the further away you are from having to make that decision.