1. If you sold the truck, or the crap, how much money would you make on the sale?
If I were to sell the truck and all three motorcycles (which have been reasonably heavily tweaked for our uses), I might get $12k out of everything if I wanted to sell them quickly. Given a few months to sell, I could possibly get $15k. They're really not worth that much (one of the motorcycles has 35k miles on it), as they're "dead brand" bikes - Buell isn't around anymore, so there isn't much demand for them. I've got a pretty good set of spare parts, and there's a lot of commonality across the bikes, so it's not hard for me to keep them going, but that's not true of someone who just buys one of them.
The truck is a '97, so it's not worth /that/ much.
The shipping supplies are salvage (I keep a large percentage of the boxes that things come in, as well as packing peanuts/bubble wrap/packing paper/etc), so I could get rid of them for free, but I'd be increasing cost-per-shipment by $10+/item for large items, or have to stop doing this entirely, which is a few grand a year income for fairly small amounts of work.
2. Where would the money go?
Probably a blend of my Betterment and Lending Club accounts. Maybe a bit into index funds, but I'm trying to move a bunch to Betterment. I might keep a bit in cash for a down payment on a house next year (planning to put about 50% down, maybe a bit less depending on how much it costs to get the septic system rebuilt and what my stock grants are worth at that point). I wouldn't be paying down any debt, as we don't have any (no mortgage currently, no car loans, just a few credit cards paid off in full monthly). It would be a small blip on Mint "available cash/investments," and a probable loss in net worth.
3. How much would your life change without the truck/crap.
For the next year: Not significantly, though I'd have a harder time hauling server racks & such, as I'm the only one in the side business with a long bed and a canopy (surprisingly useful when it's raining). I'd be unable to get to said side gig to assist with server builds and such unless my wife didn't need the car, as it's ~40 miles away (which, if I'm just heading down there to work, I'll take a motorcycle for).
Once we move: It would be a lot more difficult, as my plans for Idaho include moving 20' shipping containers around (office/lab/server rack space, experimentation with sailboat style cabins with highly space-efficient construction instead of the usual cabin in the woods construction), antique cars restoration, a project car (or parting out cars/selling parts on eBay), and possibly repairing/refurbishing construction equipment (Bobcats, light excavators, etc - I like working on engines and such). Lots of heavy things. Also, building a moderate greenhouse, aquaculture beds, and perhaps a biodiesel processing facility, if there's not a local coop I can get involved with. (no, I really don't fit in Seattle)
My wife & I take street motorcycles utterly inappropriate places and intend to continue once $kid is old enough to ride on the back (or in a sidecar - I might refurb a vintage BMW with sidecar or a Ural).
4. If the truck were replaced with a small car and a small trailer could you accomplish what you do today with the truck?
Given that I replaced a Subaru Outback with the truck because the Subaru was unable to do a lot of what I was trying to do with it (which included towing - 1300 lbs through the mountains was pushing it for that car, despite a 2k lb tow rating), it would be a poor replacement, and I would have to either store the trailer in the garage (which would mean I could not fit a car in there, even with a small folding trailer that wouldn't handle a lot of what I need to move), or store it in the overflow parking, which is currently full with no available spots. The small car and trailer would be utterly incapable of doing any of the stuff I plan to do once we move. And half the reason we're moving where we are is so we can play with that type of stuff. I intend to be substantially capable of meeting our own food/energy requirements within a few years of moving.
Now I know you like owning a truck, but you can turn this around if you want. A small car will be fine for runs to Home Depot. A trailer rents for $20 a day around here. You can buy one at Lowes for $350 to cart furniture around and keep that business going.
A U-Haul trailer of significant size is most of the tow rating of a light vehicle (and, mostly, they flat out won't let you tow it with something small - I've tried in the past). A lightweight, cheap Harbor Freight trailer is of questionable use for anything heavy, wears the tires disturbingly quickly, and is still a storage issue.
So am I picking on you for truck ownership? Yes. I've been there very recently, and you don't need it. It sounds like everyone else needs you to own one, but looking out for yourself - YOU can do YOURSELF a favour by not owning it. ANd twice a year you'll think "man, I could really use a truck for this" - and thats when you can rent one for a day.
IF you make the lifestyle changes, money will follow - after all this a board about money choices, not comfort choices. If you don't want to make a lifestyle change for better money, you should be making this post in a different community.
The cost, to me, of keeping a truck, is fairly low. It's paid for, isn't driven that many miles, is holding value quite well (low mileage 7.3s seem to be going up in price, if anything), and I do the maintenance myself, so that's quite cheap. Insurance isn't that much for it either, as it's in the "low miles/infrequently driven" category, my record is clean, and I'm married. My wife & I decided on a truck after an evaluation of what we were actually doing with vehicles, and a long bed truck set up for heavy towing made sense for our long term plans. I was frequently having to make multiple trips with my Subaru to move things (you can't fit that many 4U server shipping boxes in the back), it was a pain to tow with, and was looking suspiciously like it would need a new transmission and engine fairly soon (the previous owner utterly beat the crap out of it, near as I can tell, based on things that were failing or making a lot of noise - the flywheel had serious heat damage when the clutch needed replacement at only 100k miles, the transmission input bearing which takes hard load from aggressive starts was a lot louder than it should be, and the piston slap was pretty bad, which speaks to being driven hard when cold).
We have quite good cashflow and savings already, and live well below our means. Selling a well maintained, low mileage truck (under 100k) to buy another one in about a year would probably be a net loss of $5k+, given the various transaction fees, parts/maintenance I'd have to do on the new vehicle, and the difficulty of finding older, low mileage trucks in Idaho. And rental trucks generally don't come equipped with a 5th wheel hitch, which is pretty much required for any heavy towing (20' shipping containers are 8k lbs tare).