For a second vehicle, the 2001-2002 Sienna.
'98 - '02 are all the same body style, but the 3.0 VVT engine was introduced in '01. It's a fantastic engine: smooth, powerful, efficient -- a pleasure to drive. (wish I had it in my '02 4R Sport) I wouldn't turn my nose up at a '98-'00 if it was well maintained and the price was right, but if you can find an '01 or '02, the 3.0 VVT is nice.
Pros: dual sliding doors. Get the captain's chairs for the middle row. It's so comfortable to ride in, it will become your go-to vehicle for traveling. 4 adults seated comfortably in bucket seats. Mid-20s mpg. If you can find an XLE version, they're very nicely appointed. Leather, nice stereo, etc.. And at this point, they're pretty cheap.
Cons: no "stow and go" seats. It's a pain in the ass to remove/store the seats. Online community sucks. The Sienna forums are filled with questions surrounding windshield wiper and headlight bulb replacement threads.
I researched Honda Odyssey and Siennas when I was looking for a van. The transmission issues with the Hondas are very real. The Sienna powertrain is just so much more robust.
You're in NY, so look out for rust. It's no worse than any other vehicle (and better than most) in this regard -- and MUCH better than a Chrysler product. (I wouldn't take a Caravan if it was given to me for free... seriously, they're that bad.)
Just my 2-cents. After adjusting for inflation, still arguably worth that.
