Well, it's really a matter of taste.
While I'm a fan of the squared look of my 60, the bodywork of the 250 and 550 doesn't charm me at all (in person, though I was charmed by the photos). With the factory tire, the 2 model seemed to me to be puny. It's literally a Prado, as I'm sure you know.
It's certainly a Landcruiser, but it's a low-duty Landcruiser nonetheless. It's much closer to a 4runner than to the famous heavy-duty station wagon Landcruiser in the tradition of the 60, 80, 100 and 200. If you were to say that the GX470 or GX460 were "not" Landcruisers and ignored this model in the past, we're literally in the same place here.
At Overland Expo, during the «fireside chat» with Toyota engineers, I had the opportunity to ask a question. I asked if "THIS" Landcruiser, with its "low duty" chassis and drive train, would be named Prado, as is the case everywhere else on the planet where the 300 is also offered. The Toyota people simply told me that here, in North America, it would bear the name Landcruiser. Literally, it's North America's consolation prize for the 300's demise.
The name of the post is "From 100 to 250". So what I'm saying in relation to the name of the post is a 100 owner considering a 250 would be making a gesture equivalent to considering a 4runner or a GX460 in 2019 for example.
DON'T GET ME WRONG... it's a Toyota. It's a fantastic vehicle, capable and very reliable. I could certainly consider buying one one of these days, but right now, I'd experience a transition from my 100 to a 250 as a demotion.
Starting from scratch, buying new, I'd certainty choose a 250 over any Bronco or J33P. I'd probably choose it over a 4runner because of the "J" in its VIN.
May the Cruiser God keep me from my sins