I have a 2002 Toyota Tundra RWD with 296,000km (approx 185,000 miles) that I love dearly. I paid $5,000 Canadian for it in February, and it was in pretty good shape. No rust, clean title, timing belt recently done, and nothing majorly off at the time except for a couple exhaust leaks. You may be disappointed to learn, but I also spent about $3,500 CAD putting a levelling kit, new wheels and 32" tires, and 1.5" spacers all around (to eliminate frame rubbing). I also chose to replace the exhaust manifolds which cost about $2,000 with aftermarket parts.
Long story short, I have spent an arm, a leg, and a kidney so far (about $12,000 CAD including licensing, taxes, safety) and I love the truck, BUT the transmission started stuttering a bit in the mornings a couple weeks ago in first gear until it was warmed up, so I took it to a transmission specialist and they told me it needs a full transmission rebuild. They quoted $3,000 - $6,500 for the job. Should I take the truck behind the barn and cut my losses? Every mechanic I've taken it to is shocked to see how clean it is, but $15,000-$18,000 on a 17 year old truck makes me choke. Any insight would be much appreciated, but please be nice :)