I started reloading with the RCBS Rockchucker and ended up upgrading to the Piggyback Progressive after I learned how to reload correctly on the single stage Rockchucker. I would highly recommend you get the RCBS Rockchucker kit. I went with Lee dies, they are cheap and load very accurate ammo. You can load a box of 38, 357 or 9mm practice rounds very cheaply and if you do it right the ammo will be a lot more accurate than off the shelf ammo because you can tune the load to your individual firearm.
I'd also recommend you begin with a single stage press (RCBS Rockchucker or similar) and by loading the straight walled revolver cartridges before reloading the auto cartridges (9mm). You will learn a lot and the revolver cartridges are easier to reload.
As to the Glock, I think that after you do the detailed research you will agree that the Glock 19 is very hard to beat. Like any firearm, you need range time and training to really get comfortable with it. So, get the Glock you like and get some training and practice. Reloading will help a lot.
