I think there's a huge value in knowing your vehicle. It makes troubleshooting a whole lot easier, since you know exactly what has been replaced and when, and how things looked when you did the work, etc. Even the best repair history can't match that. You also (hopefully) have confidence in your own work that would not transfer if you sold it (think about when you bought your truck and the PO said "Yeah, I just replaced this, and took care of that, etc." - how much faith did you have that he did it right?) Both those facts mean your vehicle more valuable to you than it is to others.

Barring an serious accident, I can't think of a failure that would make me want to get rid of mine. But if had serious rust and/or body damage issues AND a major mechanical failure, then that might do it.