I recomend the Lee Classic Turret press, add a Pro Auto Disk powder measure, and the Safety Prime system. Buy a decent scale. (Digital runs from $30 up to more than most are willing to spend. A beam scale will run for $40 up to about $150 they all work.) Dies of course, and a good manual. That will put you well under $300 and leave money to buy supplies with.
For hand gun reloading I would highly recomend the turret. It is much more efficient. With a handgun round it takes 4 pulls of the lever once the dies are set up to have a completed round.
I have been reloading for two Glocks for the past year, and half. Both shoot reloads just fine. I shoot range pick up brass. I use just a standard die set for reloading. I have never had a single problem with reliability. I do stick to plated bullets though. I have not shot any lead out of them. I would also say do not buy the bulge buster. I have never had a problem with literaly over 100 thousand pieces of brass sized. Over 30 thousand of those have been fired though the Glocks. Neither has failed to feed, fire or eject a single time.