Highlanders are indeed kept forever and can be hard finds. I know this from experience. Jumped on it when I found a cherry one. Oddly though they're priced a bit better than 4Runners despite the lack of supply, but as I noted in the new 4Runner thread, 4Runners have a cult following.
Pilots were sold in larger quantities than Ridgelines, so they're easier to find. On early ones I'd for sure bypass the integrated trans cooler. I really like the Gen 1 Pilot - nice big box on wheels, the way an SUV is supposed to be. They also have a pretty good sized third row.
There are great choices from the 2000- model years from Toyota and Honda. The RX, Highlander, Pilot, Ridgeline, RAV4, CRV all exploded onto the market and for the most part have proven to be superbly well made vehicles. They also gave us revamped and dramatically improved vans. Spending $5-8K on a 2006-ish pick from those segments might be a lot for an old vehicle, but you can pick up a very high quality unit with years and years left on it.
Honestly, as my Highlander is getting close to 350K, it does NOT feel like I've added 200K to it. It's still a solid vehicle that runs and drives amazingly well.
