What's wrong with my 5 speed?
 

It has happened about 6 or 7 times now, I shift into 2nd gear and the it doesn't quite go in. I have to redo the shift and I might grind the gear (so NOT cool). Is there something wrong with my transmission? Could it be operator error (it only happens in 2nd gear) and I do feel like I did the shifts right.

Trans Oil change?

either bad synchro, bent fork, or non-disengaging clutch
or something as simple as broken/worn shifter bushing

My clutch slave cylinder looks like it might need changing. So far my transmission hasn't acted up since I posted the question. Hope to change the slave cylinder within the week.

Was it under a lot of load when you were shifting? Could be worn motor mounts.