The experience of our grandparents buying a home that they could afford, likely with one good income earner, living in it for 50 years, then making bank when then sold, is very common. But not attainable or realistic for most people in most markets these days. For many of these homes (in top markets particularly) you're either looking at a multi-generational family, or two really high earning professionals, who can afford these homes. I also find it surprising that they have not had any major repairs in 50 years, but perhaps it's what you mean by major. A rough estimate for expenses on home maintenance is 1% of the home value, though of course there are certain factors that will move that number around.
Yes, moving when you are a renter sucks, just like moving when you are a homeowner. You pay a premium to not have to move as much as a homeowner, but many people are moving quite a bit as well, seeing many of their hoped for gains in real estate getting chewed up my realtor fees and moving expenses. Most renters have smaller spaces and pay less when they move because they don't have as much stuff (and of course pay no realtor fees). You would have to move a considerable number of times compared to a homeowner to spend as much money. Being a homeowner might be more convenient, but you are paying a premium for it.
I am not saying it's always better to rent vs buy, or vice versa. Just that there are a lot of hidden factors in both cases that people don't consider. Most people compare rent to a mortgage payment and nod their head when the real estate agent says "And when you own a home you're investing that money in yourself!" as if it's that simple. The 1960s were 50 years ago. It's just not comparable any more.
Index funds are just a dead easy way to invest without ever trying to time the market. I won't go into why I prefer it as investing tends to bring out the nasty in people, but feel free to take a look at Couch Potato investing if you want to know what it's about.