I have a '97 Voyager with 160k (bought used with 37k) and no tranny problems yet. As long as the body stays decent, I keep it. I figure once the car is payed off if I pay less than an average of the car payments for a year ($3600+?) in repairs, I'm ahead. I'm way ahead. Even if you've replaced the trans twice, I bet you are still ahead. Find a good mechanic and treat him well. Never ever take it to a dealer. They will rape you.
Also have a '95 with a rebuilt trans ($1000 by a reliable shop) at 90k. Way ahead on that one, too. I dumped our original '87 died (snow belt body cancer) at 13 years. Way ahead on that one, too. The savings have put three kids through college with money probably left over.
I don't really care about new features in a car. Give me a radio that works and a heater and I'm happy. I can live without air when it dies since we don't get that many hot days. If I were rich, I might buy more often, but I see new cars broken at the side of the road every day so there is no guarantee.
Replaced the tranny twice... the second time was my fault. If you have an A604 4 speed auto you MUST use Chrysler specific tranny fluid.... and you MUST change the tranny fluid and filter every 30,000 miles. So I guess BOTH tranny problems were really my own fault.... first I never changed it (from 122,000 when I bought it until 250,000) and then I used the wrong fluid (at 285,000). Broke a rocker arm shaft at 292,000... it was over torqued at the factory. Had the engine swapped out, kept on going. Replaced the radiator twice, lots of tires, a couple of batteries, otherwise just routine maintenance.
Finally retired it as the body was rusting out too bad... northern Michigan winters will do that to you!
I do almost all my own maintenance... that way I KNOW the status of most things on the vehicle. I’ve seen all too often things that get missed by shops... they are there to do what you tell them to do... hopefully they mention to you other things that they notice, but this often doesn’t happen.
If you don’t do it yourself, the best idea is to develop a long term relationship with a good private mechanic.... and hope you never have trouble on a long trip away from your home area.
I’ve had several Dodge minivans over the years. Once, when the transmission went out and had to be replaced, the mechanic told me “these always go out between 50 and 150 thousand miles”. Always!