Is this cyclical? Does every generation think less of the next? Of course they do.

Worth pointing out: nobody hates on their own children. The 'boomers did not spawn the GenX'ers. The "Baby Boom" is everyone born after VJ Day in 1945. They came of age during the Vietnam war. The "Greatest Generation" gave birth to the 'Boomers.

By contrast, Generation X is everyone born to the generation born before VJ day. There's obviously lots of overlap, but we're really talking about two overlapping cohorts. Thus, most of the GenX hate came from the 'Boomers; most of the Millenial hate comes from GenX.

aside: We are currently debating some big questions in our household about finances and opportunity costs. Do we buy another house and put down 20% or do we rent?

Shameless plug time: one of the subreddits I rescued is /r/realestate, which was a sinkhole of SEO linkspam but I beat it back to usefulness. It's now a haven for real estate investors.

The answer to your question is complex. Large foreign blocs have been purchasing single family dwellings as rental opportunities, driving up the prices of everything under $380k. You have to understand: Real Estate has NEVER been a decent speculative investment, outside a few hapless bubble years. Real Estate doesn't even track the Dow. However, income property is a very safe and secure investment traditionally pursued by conservative investors. Anything other than buy'n'hold is a misstep.

Your mutual funds will crash, it's just a matter of time. I used to play with them and I did damn well, primarily by betting against the American economy from 2004-2009. However, current financial prospects are disquietingly tied to legislation which follows no real rules. I'm in ratcheting index funds now.

We have a property manager. There's no other way to fly. It takes exactly one eviction to make ten years worth of property management fees worthwhile. Our approach to finding one was we asked people we saw moving out who managed the property and if they liked them. When we got the same answers ("this lady" and "yes") three times, we called her up. We then let her decide what renovations to make to the place prior to opening it for rent. It cost me $6k in improvements but the place hasn't been vacant for a day in five years and we've been through four sets of tenants. I don't even know their names. The latest bunch I know literally nothing about them and I'm totally fine with that.