I wanted to get a newer van with lots of whistles over an older, higher mileage honda or toyota. That's my preferences and I suspect it all comes out in the wash as far as resale if you plan on keeping it for a few years. I would be deciding to resale a honda with 200K or a dodge with 100K---neither one will fetch me a large sum.
This is kind of where we ended up, too. We were looking at 04-07 Siennas with 65,000+ miles, had crossed out the Oddys of that generation because they aren't radian-friendly (and we're a Radian-centric family, lol). I didn't like how "stripped down" the Sedona looked, and there were literally NO used EX models in our area.
My other issue is that I really needed the telescoping pedals that the T&C/Caravan has (I think you have to get the Limited Sienna to get that) because my legs are so freakin short. I feel WAY more comfortable being farther away from the steering wheel now.
I decided that, even though the Sienna was the more 'popular' CSO choice, if I was going to have the van for the 4-5 years my loan would be for, I would end up in the same place I was in with my CR-V - a feeling of loathing for this sh*t bucket (lol). So we ended up with the 2011 T&C, which was a IIHS top pick, and had all "Good" ratings (same as the Sienna). And I got way more "features" than I would have gotten in the older Sienna - 2 brand new factory-installed DVD players, Sirius radio, that groovy touch-screen console with the buttons on the steering wheel (again, very short - it's hard for me to change the radio channels without leaning way over in most vehicles).
If we had 3+ kids, it would be a different discussion, because I would have to figure out what to do with an extra RFer, or a booster in the 3rd row that might be a challenge, or whatever. Maybe I'll grow to be annoyed with it. I've only had it 2 months, so there's no telling.
ETA: the only thing it didn't have that I wanted was built in Nav, because my Garmin is like 3 years old and all the streets are wrong, but I'll just buy a new Garmin :shrug: