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People always tell me I should be selling these things for a living because of how much I praise them, the Toyota Sienna. Of course it's going to be a little outside your extremely low price range of $1500 but just wanted to get that out there that the Sienna is the best vehicle I've ever owned.
From your choices
Dodge caravan 2.4 - it's an interference engine which means that you better make sure that the timing belt was done at the proper intervals. If that thing goes out, you've damaged the head, and the pistons (aka, toss it in the garbage. cheaper to buy another van than fix it)
Town and country is a luxury version of the caravan, feature rich but still plagued with the same mechanical issues.
Ford freestar - Yes, they have serious transmission issues, which is something the caravan/town & country don't have. You'll also feel less pull even though it has a much larger engine. Also, not sure where you're getting your specs from, but the freestar is the worst fuel economy of all your options here.
Chevrolet uplander - just my opinion, but DAMN is this thing ugly! Mechanically speaking, this is your best choice. Sure it doesn't have the high fuel efficiency of the caravan, but you're going to save a lot by not fixing the engine all the time. Unfortunately you have to put up with that horrible looking front end, I mean seriously...what the heck were they thinking.
I vote uplander. Or be realistic and put some more money on the pot and get a Sienna.
Source - Me, I've owned a car lot for the last 21 years and have seen them all come and go.
P.S. I own 3 porsches, a lamborghini gallardo, a suburban, and a 2006 Sienna; the Sienna is my favorite :P
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