I don't think it's necessarily a sign of any issues. I think it just depends on the truck and your driving style. My Deuce shifts like a dream some days, and can be downright grumpy when going into fourth on other days. I frequently have to let the clutch out just a tad to line up gears to put it into first as well. I had a 1949 Dodge 1 ton years ago, and it was the same way. I wouldn't worry too much about it until you can't get it into gear at all.