Derek,
I know EXACTLY how you feel! I acquired my 'beauty" last March off eBay and thought I'd gotten a pretty good deal at $6200. After enjoying the truck for about three weeks, the cheap black paint that the former owner (dealer) had painted on the hitch & frame began to wear off. The rusty scale on the underside is SOOOOOO bad, that I'm seriously considering buying another frame from a yard and swapping everything over. The Engine Room isn't (wasn't) much better.
Things started going bad about 5 or 6 weeks after owning it. It would stall intermittently and threw codes (I don't remember 'em right now) indicating PMD failure. So, I got me-self a new PMD with remote & mounted the heat sync on the intake.
The stalling improved, but did not go away completely.
Then my fuel mileage went to the dogs (see signature).
I found this website shortly after the stalling issue surfaced and also bought the Troubleshooting & Repair Guide, which I now affectionately refer to as my Diesel Bible. Get it. You won't be sorry.
On Christmas Eve, I pulled the thing into the garage for a planned R&R of injectors, glow plugs, injection lines and moving the PMD farther away from the engine. A buddy at work convinced me to check the compression and after doing so, discovered that #2 was down about 150 pounds. Huh-oh. Pulled the heads expecting to see blown head gaskets, but they didn't look so bad - nothing obvious anyway. Sent the heads to the machine shop.
Junk.
All eight exhaust valves cracked and bad cracks in between the valves on three jugs.
Another $700, plus the necessary extras (head bolts, gaskets).
Both manifolds were junk with holes in 'em. Add $200 more.
My down pipe was pretty, but the four bolts/nuts in the rectangular flange that bolted to the cat were completely wore down to a point. Had to cut it off. Muffler had something loose inside, and the crossover was junk. Another $400 for exhaust (upgraded to 4").
While I was poking around TDP, I found several discussions on water pumps & crank dampeners (aka harmonic, torsional). Figured by the looks of my water pump, another $45 or so was cheap investment as I already had everything off.
Both dampeners also needed replaced. Another hundred or so.
The Diesel Gods must have been smiling on me the day I checked my timing chain - it only has almost 3/8" of slop, well within the wear limits.
Everything, and I mean EVERYTHING that I have taken off the engine has had to be cleaned either via sandblasting or wire wheel and painted. (I use Rust Bullet - great paint).
Did I mention the left inner fender well? I'm amazed the battery didn't fall through. Another $50.
Like you, I have some mechanical experience and was a bit overwhelmed with these diesels. Nevertheless, the information on this site and in the Diesel Bible is fantastic and the guys (and gal) here are very helpful. Chances are your issue "du jour" has already been talked about. But don't be afraid to ask if you can't come up with something.
Manuals? I have a Chiltons Repair manual for the truck & the aforementioned Diesel Bible. I also bought the subscription to AllData, but other than the TSB's & recall info, they really don't provide anything more than the Chilton's book.
You CAN do it, man. Patience & willingness to learn is all it takes (plus some metric deep-well sockets). We're all here to help.
-Bill
95 K2500 6.5TD, Ext cab, short bed, 123K, FSD Remote, minor overhaul @ 123K: new injectors, glow plugs, glow plug relay, injection lines, heads, exhaust manifolds, harmonic damper & idler damper, water pump, (timing chain at 3/8" play) 4" exhaust, K&N air filter, CDR valve, trans cooler lines, alternator. Dead Kitty & deactivated EGR. (MPG: 11.5 before work listed, 13.5 afterwards & 17 w/ Marvel Mystery Oil)