I know a lot of people who inherited some small place from a relative and they rent it out to supplement their income and aren't anywhere near upper middle class.
What is you definition of upper middle class?
All I know is a lot of people owning property here and there without being some upper middle class. You don't seem to understand that a lot of people even if they have low income have the desire and time and are hard working to slowly build something, which in 30 years of time becomes what you call a vacation home. I guess you are not used to manual work and think is impossible to do large things by yourself.