mine does basically the same thing.I just down shift and make sure im in 1st before the truck stops. When your having problems getting into gear do you hear a clunk inside the tranny if you try to go back and forth between 1st and 2nd?
If thats the case its slack in the tapered bearings inside the tranny and it just needs to be reshimmed.
When the main shaft get a bit of slack the tapered bearings let the shaft assymbly fall a bit and it drags along the pilot and you just have to hold the clutch in and hold the shifter in 1st lightly untill it slips in.
Mines doing it and I just havent had the time to pull it to take up the slack.
sorry for the long post.