I bought a dinky little townhome in 2013, and we stayed there for 2.5 years until we outgrew it.
Built a new townhome (was cheaper to build then) in 2016 and stayed there for about 3 years until we outgrew that one.
Built another townhome that was/is perfect for our family right now (big enough bedrooms, unfinished basement, 360 sq ft of grass in the backyard).
My only regret is not keeping the previous homes and renting them, but when we moved, the possibility of having to make 2 house payments was, well, not possible. I'll probably try to hold onto this townhome and rent it out, because we're 30 years at 3%, and rent would be double what my mortgage is now.

Now, I have a brother that is 2 years younger than me. He's had multiple chances to over the last 5-6 years to buy a small townhome, but they could never find the perfect one, wanted to wait for the crash, etc.
Fast forward to today, and they're still paying rent, and if they buy they'll be at 6%+, paying 1.5 times my mortgage for a place that's 800 sq ft smaller. They're looking more than they did a couple years ago!!!?

It sucks because i want him to be successful. He's honestly ticked that a brother 7 years his junior bought a place 2 years ago. That brother was smart and got in while they could, and have made at least 75k in equity.