We are a 'drive till the wheels fall off ' family too

OP, I think you could hang on to that van for a while. A $300 repair is not so bad if you keep it another year or two. The tie rods going is not unexpected with age, on any vehicle.
Some people won't do transmissions, but I did one on my 1998 Chevy Astrovan (bought in 2005) in 2008. I still drive that van. It's paid for, and insurance and property taxes are dirt-cheap on it, on all our cars in fact. I would not put any more big money into it.
My daily driver is a 1997 Chevy Cavalier that I just put 4 new tires and an alignment into in Oct. Dh also replaced the water pump and a motor mount. This old car is great on gas and so cheap to insure.
We are going to Disney in Feb and we have chosen to rent a vehicle to drive, because our cars are old. The cost of the rental is less than 2 months car payments on something new and i'm not putting the wear and tear on my own van. For us, this works out.
For me, when a vehicle is driven into the ground is when-it won't run and the costs of repair is thousands. Tie-rods and water pumps and stuff is routine repair for any vehicle. I also choose to have
AAA, but we've actually only used the towing twice in like 15 years.
I'm not saying I didn't admire the Chevy Traverse outside Test Track, because I did

but then I looked at the sticker price and thought about how much I like not having car payments!
ps-here, we pay property tax on vehicles, and it's based on book value. It can be substantial (like, many hundreds) on a new car. I also don't carry collision on my old cars which makes our insurance cheap. But I keep some $ put aside in case a vehicle is wrecked or dies beyond repair.