Advice on what year to choose from on a 2.5 Gen Tundra?

2019+ would be my suggestion. Throwing a transmission cooler on them is a simple task and a package is sold on the site with all materials and video instructions are available. Transmission cooler is not an issue. If you can find a 2021 with all the bells and whistles for a reasonable price that would be the top shelf choice. If not consider what comes on the one you can find. I like my 2019 TRD Sport just fine, don't expect great gas mileage.

 

I changed the head units in my 2011 Taco, 2008, & 2016 4Runners, never had one issue. Aftermarket nav has always been good in the bush, and better than the Entune crap Toyota kept trying to make stick. I did it in my 2021 Tundra, so far, it's a wonderful upgrade. Just make sure you get the adaptor to use the factory antenna, because most installers will just hook up the one that comes with the HU if you don't specify.

If you find the truck you like, don't let the HU dictate your move, the market is too tough right now, that's my best advice.

 

Amen, if I didn't know better, I'd say your first name was Scotty!