A lot of it really depends on what you are planning to do with it, what your budget is, etc...
Is it a DD, or a toy?
Are you going to be doing any technical off-roading, or just vanilla boondocking/overlanding?
What mods do you want that you are finding to be "spendy"?
I am in a similar position, myself, with a similar truck and have decided, for the time being, to wait it out so I don't end up making a decision I regret later on.
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Here is my rationale, maybe some of it will help you with your decision:
My truck is an 03 2500 Quad Cab, 4x4, with the Cummins engine. It's got about 150k on it right now, so as far as diesels go it's still pretty young. I bought it with 50k miles while I was in the Marines and have been very happy with it over the years.
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Why I am tempted to sell:
1. I have since left the Marines and gone back to school. I still work full time, but currently my take home is about 1/4 of what it was while on active duty. feeding and caring for a HD diesel truck is not cheap, and my budget would have a lot more black in it with a lower cost of ownership vehicle.
2. It's getting to the mileage where the expensive stuff starts to need fixing, based on anecdotal internet wisdom. Primarily fuel system related stuff and the notoriously weak automatic transmission. At this time, I really don't have (potentially) several thousand dollars lying around to throw at vehicle repairs.
3. Moving from the southwest, where off-road mostly means desert, back to Michigan I have concluded that my truck is HUGE. Tight two-tracks around here result in TONS of pinstriping, and some trails that just aren't accessible. Soft sand is also a literal drag. I'm not moving around the country any longer, so much of the capability that made it attractive while in the military no longer applies.
4. Being a 2500 diesel with relatively low miles, it's holding its value pretty well. If I sell it the proceeds could pay for a smaller, lighter vehicle that would suit my perceived needs better, with some cash left over.
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Why I decided not to:
1. It's paid off and not having a car payment is pretty awesome. This limits me somewhat with respect to potential replacement vehicles. I do not want to be without a 4x4, which provides further limitations.
* I commute via motorcycle whenever the roads aren't frozen, which insulates me somewhat against the ridiculous price of fuel these days.
* On 35s, the truck averages 19-21 MPG. Pure highway, I average 24-25 MPG. A smaller 4x4 on smaller tires with less overall capability (load capacity, spaciousness, cargo volume, towing capacity, etc...) would be lucky to come close to matching those figures.
2. I am a professionally trained mechanic (turned wrenches in the Marines) and have done my own maintenance since I got it, so I have it's history and know what to expect. Doing my own work means that I'll only be paying for parts; my training includes working on engines, transmissions, etc... so the maintenance issue is less scary than for someone who has to pay a shop.
* A new vehicle with an unknown maintenance history is potentially a ticking time-bomb and would potentially need work sooner than later, too.
3. Much as I like to fantasize about traveling to exotic destinations and spending all of my time off road, the fact is that 95% (or more) of the miles on my truck are on-road. If I get a wrangler/4runner/similar for the smaller off-road footprint that will be useful 5% or less of the time, I sacrifice the spaciousness, comfort, and cargo capacity of the full-size that would be useful for 95% of the time. At some point down the road I'll probably get a Wrangler to run tight trails and more technical terrain, but for right now I'll stick to the trails I fit down.
4. Hidden costs add up quick with a new-to-me vehicle. I figure I can find a different 4x4 in acceptable condition for 6k or so for a 4x4 10+ years old. Figure another 1-2k in expenses doing the baseline maintenance, then add in the cost of new shocks and maybe springs or a suspension kit (depending on the vehicle and condition), new, aggressive tires, etc... and I'd easily be in the ball-park of 8-10 grand by the time I had it ready and that's before any modifications. The kicker? My truck is from the south and has spent only 1.5 winters in Michigan exposed to the salt, so it's pretty rust free for its age. Finding a replacement that's in similar condition without having to travel (not an option at this time) would either highly unlikely, or expensive. Makes the potential monetary gains in the downgrade shrink dramatically.
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The bottom line for me came with the realization that I had put selling the truck on the table as an option as a knee-jerk reaction to my changing financial circumstances. Given more careful consideration, selling the Dodge compromises a lot of what I like to have in a vehicle, without much in return. Looking purely at the market value of the truck and monthly operating expenses gets nowhere near the big-picture in my case. The only point where it would make sense to sell the truck to save/make money would be if I replaced it with a beater economy car, and that's not something I am prepared to do.
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Your circumstances are different, of course, and in spite of the outside similarities our trucks are sort of apples to oranges since mine is a HD diesel, but hopefully somewhere in that mess will be something that gives you a little perspective and help with your decision.
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O/T - Is anyone else having issues with adding blank lines to space between paragraphs? This is the first "long" post I've written in a while, and it's driving me nuts!