[Anti_Rice_Guy]

I figure I'll ask your opinions as far as a DD goes.

I drive a work truck home most days, and only use my personal truck for personal errands, going out with friends, vacation. Otherwise it stays parked at work. Capabiliites needed: 4x4/AWD, 3000 lb or better towing capacity, seats 4, can carry kayaks. Primarily tow jet ski/small utility trailers and a few times a year for a boat.
That's really about it. Gas mileage isn't the biggest concern due to a lack of use, so while diesels are awesome, it's not really a good fit. I'm not against pickups entirely, but feel that an SUV fits my lifestyle/storage needs better. My mom has a Traverse and is one of the vehicles in the running, but I'm not a fan of how it tows - it squats a lot even with just my jet ski. (yes, air bags can be added).
Currently have an 06 Explorer with 165k miles, owned since 16k. Runs great, no issues, and completely rust free thanks to being anal about keeping things clean and detailed. Obviously also have no payments, and maintenance is significantly less than what annual payments would be on a new car, but is slowly creeping up.
What are your thoughts on selling it now vs. waiting, whether to even sell it, and what would you replace it with. I love this truck, and it fits my needs perfectly (Perfect size as well for what I do/where I go). My concern is it's still worth a decent amount now, and not so much if I wait a few more years. I'm having the passion/finance brain battle going on.

I have driven the new Colorado, Silverado, Explorer, and they all ride fine (I like a stiffer ride). I would be getting an NA V6, since I don't want the TT Ford, v8 silverado would be overkill but would be fine if I got a steal.

I would obviously price out used versus new, but would likely lean towards a 2 year old used vehicle to let someone else take the depreciation hit.

Go!