My last three vehicles have been an '02 Tundra Access Cab, a '99 4Runner, and currently an '02 Tacoma Double Cab, save for my 4Runner being a different generation I've kinda been where you are wanting to go. Before any of these it was a 2000 Tacoma regular cab, so I've been where you are now also.
I'll admit, sometimes I miss the simplicity of my regular cab Tacoma but with a wife, child, and two dogs I can't go back there. I liked the interior size of the Tundra, it was nice to have a little extra space in the front seat. I had the bench seat with the folding center console, I really liked that setup and I could reasonably carry 6 adult passengers for a few miles when shuttling for hiking and/or canoe trips. Having a larger bed was nice too but with the cap on it sometimes it was hard to get gear near the front of the bed. The biggest issue with the Tundra (for me and my wife) was the size. Wider, longer, and the terrible turning radius was the worst. Really, the turning radius was the biggest issue. The lack of after market options has been mentioned. I just bought some things for the Tacoma and it was a completely different experience than it was for a Tundra. Also, it never really seemed to have the power of a V8. Sometimes I still miss it though, a solid truck that ticked a lot of boxes.
We test drove a V8 4Runner and it seemed to have more power than my Tundra. That probably had more to do with the fact it was an '02 Tundra versus a newer 4Runner. I liked it but it was going to be my wife's car and it didn't tick all of her boxes. As for your situation I don't know, but I just don't like the idea of all of my gear being in the vehicle with me. I liked the 4Runner alright, but I need something that I can use around the property for truck work and I couldn't load brush or mulch or dirt etc. in the 4Runner.
After a few months in a '14 Focus ST I decided I needed to get back something that was practical. (If I had trouble around the property with a 4Runner the Focus certainly wasn't going to help. I got tired of borrowing trucks.) I thought about V8 4Runners, Tacomas, Xterras (I had an '04 in the past) but I kept being pulled back to a Tacoma. I never even test drove a 2nd generation though they crossed my mind. I headed straight for the 1st generation and found a decent example in Atlanta that the owner listed here. A 13 year old vehicle that certainly held its value but I'm happy. A big enough bed for all the work I need to do, enough towing capacity to just barely do the work, enough seats for the family. I can load the truck with fruit trees and two 55 gallon barrels of water and stay busy driving through fields and ditches all day. I've read in trip reports where guys with 5ft beds use the bed extender to their satisfaction. Driving it feels like I'm back in college driving my 2000 regular cab but now I have so many more options for passengers. I'm just comfortable with it.
For me my Tacoma fits the bill. The only area it might remotely come up short is in the power department but that's a concession I'm willing to make. I can't comment on the 2nd generation Tacoma but it doesn't check the $10k box, especially with 4 doors.