Current van is a 2002 Chevy Express window van. It started life as a crew hauler for the highway department. I got it six years ago, and it had clearly lost a bunch of minor skirmishes with heavy equipment, and then had been fixed with slowly declining competency and interest. It's got 145K on it now, and has one back seat. The rest is cargo space. It no longer smells like crushed aggregate and cheap cigar smoke inside, too, so there's that. It is a great van in nearly all ways, and I would expect it to last at least ten more years and at least another 100K miles, whichever one came last. The reasons I'm considering replacing it:
1. It gets 14mpg in town 18 (almost) on the freeway on long trips.
2. It doesn't fit into parking garages and barely fits in most parking stalls.
3. My wife won't drive it because it is too big.
4. I don't need as big a van, since the bed of a first generation Transit Connect is nearly as big as the cargo bed of the current van. I never pile things to the roof of the Chevy, and probably wouldn't in the Transit Connect. But, I could if necessary.
5. The Chevy has a pushrod 305 engine, which means it's a gutless wonder - the Transit Connect might be noisier and busier getting up to speed, but it won't be any slower. And, if I want to go fast, I ride the motorcycle.
6. The Chevy is dark green - you can't miss it, and nobody ever does. I can't tell you how many times it has been hit. Its bodywork is a whole lot nicer now, thanks to other people's insurance, than it was when I got it. The Ford is white - ugly but really visible. It was damaged because somebody put it in neutral and didn't set the brake, so I'm told. It rolled into a barrier, which broke a headlight and bent a fender and the hood.
There are reasons to keep the Chevy. It's paid for and I could buy a whole lot of fuel for the difference in price I'm likely to get for the Chevy and purchase price of the Ford. The Chevy is dark green with blacked out windows and looks pretty nice in a slightly sinister way. Never mind the surface ripples. The Ford is butt ugly, white, and looks like every other road slug that's in your way. If there's any underlying damage beyond the headlight and some superficial sheet metal, I won't buy it. If it's just some bent metal, it will go to Maaco and get a couple tons of Bondo or whatever they do. I have only seen pictures and haven't looked under the hood to see what's behind the damaged parts. Maybe no problems, maybe a lot of problems. So, there's too much information. Maybe I need an Edsel.
Can't go wrong there (unless you're a Coug.) 
