Criteria for a new(er) vehicle

I have two criteria.

The first is the age of the car itself; when it reaches 25 years from the date of purchase, it's time to retire it and move into something new.

The second is an engine or transmission failure necessitating replacement. I would find that highly aggravating, as my wife and I drive few enough miles that mechanical wear as a cause of failure is highly improbable.
 
When it becomes a money pit, I get bored, or life changes

Examples:
2011 Forte Koup, got bored and traded it for the Durango
2011 Durango, became a money pit, traded to get the 300
2012 Caliber, sold to get the Grand Caravan
2016 300, added a 3rd (and surprise 4th!) kid to the family and moved to an area that gets significantly more snow, being so low to the ground resulted in me plowing snow with it often, traded it in to get the truck… and with home improvement projects it’s just so much easier having a truck.

Now I want to trade the van in for a used Suburban/Yukon XL/Escalade because I hate driving the van 🤷🏻‍♂️
 
I have a lease car for work that gets turned every 3 years or so. Basically always in a newer vehicle in that regard.

Wife’s/family vehicle we usually end up getting rid of around 200K miles or 10 years. That is about the time she is ready for a new vehicle and the bigger repair expenses start to pop up.

We never used to purchase brand new personal vehicles, but we did with this last time with the Sienna. Likely will buy brand new again. We both liked it.
 
1. Standard tires should require a home equity loan to replace (owner's manual should recommend replacing all 4 if one is punctured)
2. HP must not be under 500
3. Torque must be higher than HP, preferably 600 ft lbs minimum
4. Must feel prestigious when parking around peons
 
I have been nursing my 98 Expedition and can't seem to let it go.
250k miles plus on it. I always fall into that rabbit hole of rather spend a few hundred to fix it than get into a car payment.
Now AC is leaking (quoted 1500 to fix) Need 4 tires...Another 800.00, rocker panel rust is creeping up to where it is noticeable now, doesn't tow well for our rv needs, but does do a good job towing the boat and I am chasing a trans solenoid code.
Starting to put more time and money into it, when I could be spending that time either enjoying life or working making money. A lot of stress when it breaks and the wife's nag factor is terrible when she has to use the backup car. This is the WORST part. When it breaks now, I want to drive it into the ocean with me in it.
Interior is in great shape and overall looks nice on the outside and does well for everyday use but I think it is finally time. Unfortunately, this market is not the best. I didn't realize how painful 8%+ interest is until I start calculating how much that is over the course of 5 years on a 30k+ vehicle.
Maybe I will fix it and demote this one to the backup vehicle.
 
What are your personal criteria / signals when to determine that it is time for a new(er) vehicle.
The last vehicle (about a year ago) that I parted with was a 1952 Dodge PowerWagon. I replaced it with a 1953 Willys. I recently found a 1955 that I wanted but that deal fell through. I have NO interest in any "new" car.
 
When I have a different need, I rarely buy the same kind of vehicle just to refresh. Last time I got a "wagon" to replace a sedan, or a minivan to replace a sedan, etc. Regardless of what I buy the most important thing is reliability and easy to maintenance. I expect oil change, ATF, belt, water pump regularly but not things that break unexpectedly due to poor design. Want to just change oil and regular stuff for 20 years and 250k miles is a must. Oh, need to be close to best in class mpg as well.

If Tesla is as reliable as Toyota I'd consider it, not quite there yet.
 
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