Hello everyone. Thanks for the responses!
There aren't many large hills where I live so I don't really have to deal with using the e-brake. I usually roll back only a tiny bit so it's not too big of deal. Sometimes I do forget to rev the car more though, and get close to stalling it. I hadn't thought about the shift from 1st - 2nd being difficult because of mechanical wear, it does seem to be the only shift I have trouble with. I don't ride the clutch, but I do have to coast around with the clutch in or feather between clutch and 1st alot because of how bad traffic is around here.
An example of shifting from 1st to 2nd and why I have trouble. I generally rev the car up to around 3-4k in 1st and then shift to 2nd, this requires holding the clutch at the engagement point for about half a second, maybe less, but if feels like if I let it out too fast the car lurches forward. Shifting at a lower rpm seems to make it harder to shift to 2nd and then the car usually has no power by that point. I can make clean fast shifts at any other point. I also can't start the car from a stop terribly fast. I usually have to go slow.
I also have a lot of trouble preventing lurches when downshifting. I drive this car everyday, so I'm getting better everyday, but still far from perfect.
That's my car, 1991 300zx Twin-Turbo. It has a little over 100k miles on it, drives really well in my opinion. The only problems I can notice is that it seems to idle pretty hard when I start it in the morning. In fact I stalled it this morning pulling out of the garage, because I have to go extremely slow due to having a steep drive way. The car is 100% stock.