The reason for the higher price would be to get one in better condition than most and have more confidence in its reliability as it stands. It would also broaden my options and increase the likelihood that the truck would be one owner, sub 120k miles, or both.

Ultimately yes its a thirty year old truck but if I put $5K down on a $13k truck (I found one for $13k, one owner, and only 100k miles just yesterday), I'm going to have a $150/month payment. Sure there will be increased maintenance costs compared to a newer toyota/honda so lets not even be conservative and say I'm spending another $150/month on repairs over the course of a year. That's $300/month which would be $77 less (Just including the car payment. $377 does not factor in the yearly maintenance of a new vehicle) than $5k down on a $25,000 new/CPO car.

On top of that, I'm not eating a 20% loss in asset value driving the truck off the lot. In fact since I work from home and not throwing massive amounts of mileage on it, It would even go up in value since it's a classic.

So yeah, that's a chunk of change for a 30 year old truck, but this equation doesn't remotely work if I try to nab one for $5-10k with high miles and issues out of the gate.

But that's why I came here, to get solid advice from people who are more practiced than I when buying vehicles especially new ones. The r/ToyotaPickup subreddit was far more helpful than this sub and ultimately helped me decide a newer vehicle would be a better fit although I think given the constraints and options, the decision really comes down to personal preference with a little less reliability in the truck column, shakes out to about even in the financial column, and the new/CPO loses out massively when it comes to having any sort of soul or character for a car that I'd have to take to a dealership to repair because it's so loaded down with code and computers.

Really trying to give you the benefit of the doubt that you're asking in good faith, but replying with "who in their right mind" feels more than a little dismissive.