I'm trying to figure out which is the safer bet, all other things being equal: an 05+ Tacoma with general mechanical issues, or an older Tacoma which would be subject to general wear and tear. Which do you think would be the wiser purchase assuming blue book value, and why?

 

I had a '97 Taco, 2.7 X-cab and really like it. Had an '05 Taco DC, TRD off road. Liked it too. Both trucks were bought new. the older tacos are racking up miles, they had the massive frame recall/buy back.
That being said I would buy either truck again, I liked the room that the '05 (3rd Gen Taco) had.
As far as resale, they both seem to be holding decent market value in my area (PNW)