As far as age, I worry about getting parts, if I break down someplace away from home. And getting competent work done. But then again, I bought a low-selling truck. Probably less of a problem if one sticks to the big 3.
Friends of mine have the same Tundra as I do, and I hitched a ride, and was a bit dismayed by how little space I had in the back... 4 doors but abbreviated. Works fine with little kids though, mine have yet to complain. But as JHZR2 points out, infant seats are huge. You'll need a true crew cab to fit those suckers in. Now I'm not sure what is better for the back: bending over to put kids into their seats in a sedan, or holding them up. But I do know the kids had a hard time climbing up and in once they were mobile but not particularly tall.
I would not want one of the suicide door extended cabs. While they work... I don't think I'd be very happy.
Anyhow, bed size is the tradeoff with door size. Or can be. I decided that short rear doors was ok, but that I really wanted at least 6' for a bed, when I was shopping. The setup works for me, not hauling lumber often. I consider it my overgrown station wagon. Seating for six also. When I daily drove it for a bit, it was nice to toss stuff into the back seat, just like I would for a sedan.
Hands down, it's the worst vehicle I've ever had in snow. I consider 4WD pretty important in mine; yes it will get around in 2HI, especially with good snow tires on it. But it's way better in 4HI; but its heft is still there. Which gets me to my final point: primitive part time 4WD sucks in sedate pavement usage, as it binds on every turn. With good snow tires on snow it will bind in my driveway; it binds with all seasons on dirt too. [Forget about using 4WD on pavement, ever.] It's a compromise that I put up with, but sometimes I wonder if I'd rather have paid for a different truck that had a better transfer case. Or gone Ridgeline instead.