1st Powerstroke..lots of problems

[daytontech]

Hello from Dayton Ohio! I am new to the forum, the amount of information here is unbelievable but i cant seem to fine exactly what I'm looking for and I'm stumped. I just picked up a 1995 F-350, auto tranny, 2wd crew cab with 247xxx miles on the clock, this is my first diesel btw.

So here is the story.....
Was looking for a good work truck that i can run between Dayton, Columbus and Cincinnati Ohio, 600+ miles a week. By trade i do Commercial HVAC and refrigeration with plans of going into business for myself. I found the F-350 on Craigslist, the guy lives about 40 miles away and he drove to me, I test drove it and everything was good. He brought it back the next day with title, made the purchase and parked it.

Next day....

Got in the truck, started up fine, let it warm up to operating temp, went for a drive and this is what I've encountered.

Transmission:
I never drove above 50 mph, it was city driving and intermittently it wouldn't shift from 1st gear till almost 3K rpm, after letting off the pedal it would shift to 2nd and so on. It would shudder at times and while at 40 mph it would downshift, then slam into O/D while trying to accelerate. Then all of a sudden it would shift fine, like i said intermittent. About 2 miles from my house, the O/D light started flashing non stop, CEL came on and when i came to a stop, it wouldn't take off in 1st gear as if it was in 2nd or 3rd, I tried to manually put into 1st but it was if it was still in 2nd, then all of a sudden a block from my house it went back into 1st after a stop.

Engine Prob 1:
When i pulled up to my house where the truck was parked the street had a great deal of oil/diesel on the ground. Found diesel dripping from somewhere above the starter area, it is dripping off the starter and by the flywheel inspection cover and i couldn't pin point the location. Found oil dripping from the cradle area, didn't find any leaks by front or rear seals that i could tell, it looks to be coming from somewhere near the middle of the oil pan.

Engine Prob 2:

15 min after i got home and parked it, went outside to start it and it just cranked and cranked. Shot some WD-40 in it and started right up and ran fine. Turned it back off after idling for about 5 minutes, tried to restart it and again it just cranked and cranked, used WD-40 and it fired right up. It wont start without using WD-40 when the engine is warm. I let it cool down for a couple hours and it fires right up.

I've never worked on a diesel but ive always done 90% of all work to my own cars, from tranny and engine swaps to suspension. I'm looking for some advice on where to start the process of elimination.

Thank you for your time and help

[stroken out]

as for fuel leak check drain valve on fuel bowl the o rings are comman leak. the only oil leaks i have had are the ccv dog house o rings and the dipstick where it enters the oil pan both common

[erics diesel]

Check for the leaks in the engine valley there is a drain hole in the passanger side back of the block to let it drain down. As for the oil check the pan where the dip stick goes in they are also known to leak

[daytontech]

Thanks for the helpful information, Here is an Update: The drain valve was leaking so i ordered the whole O-ring kit from dieselorings and replaced them all on the fuel bowl, no more fuel leaks! The no start when warm was caused by blow O-rings on the IPR, replaced and problem solved! The transmission issues was electrical related, replaced wiring harness to solenoid block, repaired a few wires, shifts fine without problems so far. I'm down to an oil leak coming from the front of the engine passenger side, it literally drips only while running and looks to be coming from behind idler pulley that is under the alternator??

[351fifty]

Isn't the hpop there? Check the hpop res and lines for the leaks

[daytontech]

I did check ccv and dip stick for leaking oil, it wasn't completely dry but nothing significantly leaking, no dripping. I can see it dripping while running from behind the idler pulley passenger side, it drips onto the cross member and flows down from there

[daytontech]

It was pouring rain today, tomorrow ill double check the HPOP, lines, etc. The valley is dry now that fuel leak is fixed, i did inspect hpop while fuel bowl was out and it was dry as well as lines but i could have easily overlooked something