Ive already spent 30k of my own money with down payments, taxes and upgrades towards the vehicle. Bought it for 55k'ish before the taxes.
Not intending to be a jerk, but you probably have some harsh life changes coming to your life, in your near and long term future - most significantly with money management/spending habits.
The only thing(s) you can count on is Death and Taxes……
In actuality, on a $60k truck purchase, you spent $16k in downpayment, $4800 in taxes = completely unavoidable when buying a vehicle, especially from a Dealership.
So the remaining $10k you spent on upgrades = money you probably should “not” have spent, and certainly you can simply no longer afford to spend, given the life story you provided - chalk that up to a $10k life lesson.
With that in mind, and given your impending probable medical retirement income of $40k/year, you are very likely going to “need” to move again, to a more affordable location for rent & living expenses. Suffice it to say that the cost of living has gone up everywhere….
Your ”I want(s)“ will become “what are my actual needs” in the very near future, unless of course you find a path to a new profession earning at or near your current earning potential, until “normal“ retirement age of 62, 65, 67……barring some golden parachute type early retirement offer.
Retiring at 45-46, you are literally and VERY significantly cutting off your statistically highest earning years, and the top 20+ years at that…..
RE: Given your desire to significantly reduce your vehicle financial obligations - In my humble opinion, the best choice you could make regarding your current vehicle(s) would be to: A) Take the Vroom cash-out offer on your 2022, and walk away, and drive your old Chrysler 300 until the doors fall off….or B) Sell your 2022 outright (private party) and hopefully take home a bit more cash than the Vroom offer…
Selling the 2022 truck to buy the 2018 truck is simply a bad choice/option at this point, as a previous contributor offered with great money evaluation and comparison.
If you absolutely “need” a truck, and here is where you MUST be honest about “need” versus “want”….. the only choice that would make sense “to me” would be for you to take the cash from the sale of the 2022 truck (to Vroom or otherwise), and buy a replacement truck with that cash, with no further or additional financial loan obligation - and yes, that would mean getting a truck you “need”, not what you “want”…..
$1200/month for a single truck payment and insurance is crazy to me, but in this day & age with vehicle prices as they are, this seems almost normal…..
The truck payment is what it is, unless your credit is so bad that you are getting clobbered with a ridiculously high interest rate…
If you have good credit and you initially took on a higher rate to buy the truck, or maybe you can simply lower the loan interest rate elsewhere - apply for refinancing at a lower rate (local Credit Union, whatever institution is offering the lowest industry auto loan rate(s) - check USAA, Navy Fed CU, etc….)
It sure sounds like you are paying WAY too much in vehicle insurance - SHOP AROUND for auto insurance! Do NOT be afraid to take your insurance business elsewhere….Over the years I have had vehicle insurance with = AAA, State Farm, Geico, Nationwide, & USAA, and every move saved me significant money. You mentioned VA benefits - Call USAA for a vehicle insurance quote!
*Take your 2022 truck in and get ALL of the issues fixed under warranty at a Dealership - get a loaner from the Dealer or get a rental car…..do what you gotta do.
Best of luck to you