My situation is similar, been limping along my '91 trying to find the right replacement. Actually bought a 2001 Tacoma about 2 years ago now and that turned out to be a debacle. Cleaned up some title mess, fixed some things, put in cruise control (this is something we'd never really had and still don't). Ended up needing quite a bit more to bring up to even with my current truck and that was a financial impossibility at the time.
So I never got around to selling my truck because the Tacoma was being worked on more than driven. The only thing that was hand's down better was the engine. Ended up selling it for less than we paid for it and since then we've been very reluctant to consider another vehicle. Being very selective and this eliminates all but a few candidates. Basically at this point after driving nothing but used vehicles my whole life I'm tired of buying someone's problems. I figure if I get a new truck and take care of it I have to expect be able to get the same service life from it.
We'd probably not tie up any savings in it, with interest rates so low I'll just take the cheap money. Probably a 36 month or so loan at 0.9% or less. But it's a long term prospect, which is the root of why I want something fairly simple without a bunch of things to fail or become unobtanium. It would stink to have a 15 year old Tacoma that runs fine but I can no longer get a window switch or some long since discontinued controller that leaves the fancy center console mission control thing a useless black screen.
I'm also being realistic. As much as I want a Hilux or Ranger, those are not available. But my need for something that can travel highways and back roads and carry my junk is. So given what's on the market, has a warranty and can be titled and plated, the Tacoma still seems like that only choice. So unless Toyota really, really, screws it up, there it is.