I find with these things, literally .. +$10 each time adds something I will want. Like with my soldering iron, I started with a pencil with no nothing (control, even holster) and wanted a good one.
$10.. holster
delta $10, variable power
delta $10, variable temperature
delta $10, digital readouts
delta $10, Hakko FX-888!
So I usually go for the best I can get before it goes to steep prices..(got it for $90 somewhere local, I mean it is QUALITY, has many clone/real parts everywhere to buy, so its value was worth the bunch)
DMM I just settled for something Dave listed in the $50 shootout. My radioshack was just too crummy most of the time, integrated current and voltage leads, manual ranging that was really stiff.
I suppose the lesson here is: Buy the crappiest first so there is less risk..and you know what you want, if it is cheap. I wouldn't buy a $99 new power supply for example.. too risky for the price even if it is 'low'.