I know a family who goes multiple times a year and has since the kids were infants, but they bring their own parents and siblings with kids as well, so there is some switching off. They are teacher in NJ, so are now also limited to when NJ schools are out. I think they're nuts, but they have extended family and they do coordinate their vacations, so more power to them.
We have never taken a Disney vacation with other than our stereotypical 4 person"nuclear" family, aside from the marching band trip when they were older.
Sometimes I wish it happened with family members, but it didn't. I did meet my brother's family for a day once, when a business trip coincided. That was kind of cool.
We waited until both were able to walk all day. We stayed at value resorts, so the time to go back to the resort for a nap or whatever was simply not worth it, thus commando style. Getting a car was the best decision for the evenings, but that was before they started charging resort guests for parking. No other people, car a/c, our own music ( or just quiet!), no waiting for a bus...it was lovely.
Do an internet picture search for "huge kids disney strollers", then try not to come back here and rant about it. ( I struggle
![Wink ;) ;)](https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f609.png)
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A lot of the problem comes from the footwear the kids are wearing. Flip flops, crocs, no socks. Another part is all of what I would call enablers in videos and other "tipster" web sites and books touting the best way to do Disney is to rent a stroller for your kid.
IMO, if the kid needs to bend their knees so their knees are higher than their hips for their feet to be on the stroller footrest, that's way too big, barring of course a legitimate disability.