I playted for ~10-12 years, but quit about 5 years ago due to time constraints and a general lack of interest by my friends.
At the time I played, JT had some of the best masks out there, some of which were designed specifically for people who wear glasses (the sprectras, I believe)
No matter what mask you get, don't go cheep on the lenses. Get the dual-pane "thermal" lenses. Anything lss foggs like a mofo, for me. Also JT makes a fan that attaches to the top of their goggles and moves air through the goggles. Airflow is very important to keeping your goggles clear. Evenwith thermal lenses, I could fog my goggles on hot, humid days, if I stayed still for a period of time. Usually they would clear up very quickly when I started to move again.
Guns:
It's really hard to go wrong with Tippmans. They're built like tanks and stand up to a real beating. A field I used to ref on used a lot of Tippman Pro/lites and they were rock solid. We put very little maintence into them. As with ny Tippman, though, you'll want to replace the barrel. Somethng like the flatline or a DYE Boomstick will make a huge difference. (people seem to be split 50/50 about the flatlint, where most people who own DYEs seem to love them. Personally, I 've shot a Mod98 with a flatline and I was very impressed.)
You might also consider a Smart Parts Ion, if you're going to play regular. I've been thinking about getting back into playing and the Ion is a top contender on my list. It'll cost you more than most Tippmans, but they come with an impresive feature set for the price point. (They can be had for just under $300). Of course, the Ion would benefit from going low-pressure, so you can get into a couple hundred in accessories fairly easily. (Nitro tank and electronic hopper, mostly)
Rate of fire sems to be one of the important features in speedball and the Ion is capable of rate of fire in the 17 balls per second range.
http://www.smartparts.com/Products/Ion.aspxI'm going to be really torn between the Ion and an A-5, if I decide to get a new gun.