...My questions are: Even though this may be a clean, maintained rig, how is it worth $20k? I understand that some people are willing to pay that, but that does not necessarily correlate to true value... I may just be naïve.
The average Joe sees it this way...
Time doesn't do near as much damage as wear and tear. A 20 year old truck that's been driven very little will have some issues obviously,
but no where near as many as a 20 yr old vehicle that has been driven daily and racked up 150k miles.
Most people associate low mileage with value.
Just because you say your 3rd gen with 139k miles is well maintained, doesn't make it so, for most people that means it's ready to break down
or the timing chain is about to go out, maybe the tranny is on it's last leg. Maybe it will last until 200k, maybe not.
Add in the fact that the vehicle is a Toyota and most would assume this 20 yr old vehicle will be just as reliable as 2 yr old truck with the same mileage.
Just saying, that's how most people think.
Also, keep in mind that some folks just prefer the look or specs only found in older models.
For example, if I was going to buy a Rav4, I wouldn't buy a new one because all they offer is a wimpy 4 cylinder. the newest one I would buy would be a 2012, because I like that motor. That was the last year they put the V6 in it, which made 270 HP, which is a beast for an suv that small. And since I would be looking for an older model Rav4 with "low miles", I would be willing to pay a premium for that.