Just my opinion, but to the OP, if you're shooting 300 rounds a week consistently, reloading even for 9mm would cost a fair amount less than shooting factory ammo. Unless my math really sucks, (which it does at times), I've calculated that I save about $3 per 50 rounds(147grn). Shooting 300 rounds a week, that'll save you about $18 per session. Multiply that by 4 if you shoot every week, and that's $72 a month. It wouldn't take very long (maybe a year or so) for you to get back the money you put into reloading equipment (not counting bullets, primers, powder), and that's if you went with a progressive press instead of a single stage. Single stages can be had for a lot less, but if you can afford it, you may want to look into a progressive. I'm not sure how long it takes to load 300 rounds on a single, but I know it takes me less than an hour, (taking my time) to load 300 on a progressive (I use a Dillon 550B). That leaves a whole lot of time for the other stuff I need to get done.
A lot of experienced people will say to start on a single stage, but a good progressive press, and good safety habits, can be just as safe while being a lot more efficient, especially for pistol cartridges. If you're on Oahu, you may want to take a ride out to WGS and talk to Joe and see what advice he has. I picked up my Dillon 550B from him, he's a great guy to deal with. I'd definitely recommend reloading, especially with your round count and the fact that you're considering getting into other higher priced calibers.