98 300tdi and the symptoms are.....
A rattle on start up
Juddering when pulling away in 1st
A whirring/chattering on tickover until i press the clutch pedal, then it dissapears
A grinding feel when i press and release the clutch when driving
Stationary in neutral pedal is silky smooth, any gear engaged and it grinds

Does anyone have any ideas, or similar problem in the past?
I was thinking thrust/release bearing, master or slave cylinders, clutch damper or the actual clutch itself.
If it turns out to be the bearing, would it be best to just change the clutch assy while im in there?
Lastly, how difficult is the job and how long should it take?

Thanks

you could try bleeding but sounds like you need new clutch kit, and drain oil on gear box it sounds like baulk rings are poor too should be difficult in that gear stick jams not grates

Ive tried bleeding it down, but i manually have to lift the pedal back up making me think one of the cylinders is shot. The gears sometimes crunch in, esp 1st 2nd & 3rd but ive always put that down to a required oil change on the box.
Ive never touched a clutch or gearbox on anything, i've never needed to.

Do you have any reccomendations for a decent make of kit?

stc8358 bb ,ap (borg and beck clutch kit )

I had similar problems when I had a Tdi. That was clutch release bearing collapsing. New clutch sorted it all out (including new bearing). Rattle you hear is bits of bearing, which stops when put under pressure as you depress clutch. Mine fell to pieces when we opened it up.

Cheers!