You should be able to bang shift the transmission at redline without grinding. The trans may not shift smoothly, but it should not grind. Not recommended to do so, but a trans with properly function synchros shouldn't grind.
Most likely your synchro is going out. I drove around with busted synchros on every gear besides 5th for a year+. You have to learn to match the speed when upshifting and rev match downshift. On downshifts, I usually just push to neutral, rev to the correct speed, clutch in, and then push into gear. Keeps everything smooth even when I essentially had no synchros. If you give the synchros no work to do by matching speeds, whether they are there or not does not matter.
I ended up swapping my NV3550 since I was moving to the city and no synchro driving in traffic just doesn't work well. If you end up swapping the transmission, get it from somewhere reputable. I ordered mine from JeepsUnlimited in Colorado and it is not a good transmission. Pops out of 4th on deceleration and pops out of second in 4low.