1. Get carbide dies. No messing with lube.
2. Win 296 is the powder for performance. I have problems with it because it is so fine grained. It jams up my lee perfect powder measure. If used it in my RCBS and that leaks too. It also isn't good for anything but full house loads.
So I plan on trying something else. Acurate No 9. is on my list, but that may be fine grained too. I use blue dot in my cast bullet loads. Alliant has their new 300MP that my be worth a look.
3. If you use jacketed bullets, you may not need to expand the case mouths. I usually dont.
4. For plinking, target shooting, the cheapest bullet is probably the best. There is nothing wrong with cast bullets for this. This will affect your powder choice too, because there isn't any need to hot rod loads for paper and tin cans. Cast bullets can be shot full house, but that probably requires a gas check. So most of the time cast bullets are easy to handle and fun to shoot.
5. I don't know how many loads you can get, but I've loaded some brass 4-5 times and I'm still using it.
Reloading pistol rounds is easy and quick. It is nice not to have to wipe off lube. Trimming is probably only necessary if you crimp.