2000 V6 Dakota, Manual Transmission, 97k miles.
Engine off: Will go into any gear, but it doesn't feel like its going into to 1st gear all the way.
Engine On: Will go into gears 3-5 with some difficulty. Got it into reverse with a large clunk sound. If I build the revs and then press clutch, still won't engage 1st gear, but the truck would slightly creep forward.
Vehicle ran perfectly fine yesterday. Had a similar problem a few months ago when I parked on a very slightly decline and a gear wouldn't disengage for a few minutes.

Any suggestions would be very appreciated.

 

The truck should NOT creep forward when the clutch is depressed. I'd be looking at the clutch master or slave cylinders for a start. How's the fluid level?

If the clutch isn't releasing properly it can make it difficult to get into gear.

 

I have been unable to asses the fluid level, but there is some fluid on the bottom of the transmission case (more than I would expect).

I've read to check the levels by removing the fill plug, but I'm still trying to loosen this.

 

It's an hex style plug, on the side of the case, passenger side. It should be the NV3500 in your truck.

 

The challenge is that the the plug has a hex interior, but the outside is smooth and I have nothing to grip.

Picture of what I beleive is the fill plug. Drain plug on the very bottom looks the same as this.
http://imgur.com/gTOZdgF

 

Pick up a hex socket for it, then you use a ratchet to open it up.

17mm if memory serves.

 

Yes, 17mm. But weren't you talking about the clutch fluid at first? That would be much more likely to cause the problem than low transmission fluid.

 

Wow that thing looks like it hasn't been cracked open ever!!!

Looks like trouble to me almost no depth for the wrench to grab

My manual AX-15 fill plug was a bitch to get off all the time no matter what I think it was because they used an aluminum washer on it and the aluminum just grabbed it like crazy glue

soak it with WD-40 or other for a day or two

 

I still think it's a clutch issue but it seems he may also be low on tranny fluid. Then again, the fluid coming out of the tranny may be from a slave cylinder leaking.

 

That's kinda what I was thinking.