I've seen the Hakko FX888D come highly recommended here on the forum by some folks that do a fair amount of soldering. It looks pretty good to me as well, and seems rather reasonable at about a hundred bucks.
I've always used fairly cheap soldering irons and had pretty good luck with them. The downfall of those radio shack 30 watt types is the junky tips they have that start to disintegrate after a short while. other than that they will put up with being plugged in for hours and hours... unless the design has changes in the last 10 years, which is possible. the key to these things is keeping the tip clean if you want it to last any sort of reasonable time.
Currently I'm using a fairly cheap adjustable, NOT constant temp Velleman iron I picked up at Micro-Center. For $30 it does everything I need it to for occasional tinkering. I have no idea how it will hold up with heavy use, but I'm happy with it's performance so far.
When it comes to soldering anything thicker than 16 gauge I recommend using a larger soldering gun such as the Weller 100/140 model, or my favorite gun, the D550 200/250 Watt gun. this will make your life a lot easier working with large lugs on big toggle switches or soldering wires to track or bus wires, and because it heats quickly you are less likely to damage things.
JGL