I used my $15 Proctor Silex basic iron for the first year or so of my renewed interest in quilting. But, since it was clear that quilting was going to stay in my life, I was sucked into the belief that I needed a new iron. I ended up purchasing a Rowenta -- thanks to QVC and a persuasive on-air sales person. It was OK, but I never thought it got very hot, didn't put out good steam, and its auto-shutoff cycle was sooo short. After a few months, I reverted to my Proctor Silex.
Then, one year, my mom gave me a new cordless Maytag iron -- you know, the one that Marianne Fons and Liz Porter were promoting on their TV shows. Definitely not a cheap investment. And, yes, it is very nice to not have to deal with the cord -- especially if you are pressing a full quilt. But even it failed to live up to the hype. Within a year, it started to seep goo from the iron's "joints".
So, I trolled some of the sewing bulletin boards to see what kinds of irons people were recommending. There were the Rowenta fans, the fans of the older, heavy, classic metal irons, and some were recommending brands I'd never heard of (and available for equally outrageous prices). In the end, I decided on a mid-range Black and Decker Digital Advantage iron (think I paid about $35 on Amazon). And so far (after about 6 weeks), I really like it. It's light-weight. It heats up quickly -- even if it has timed out. It generates good steam. And it didn't cost an arm and a leg. My only complaint -- and this is hardly worth mentioning, is that because it's digital, when you turn it on you have to set the temperature. Whereas with an analog iron, all I did was turn on the power strip it is plugged into and the dial setting was already set to the temp I needed.
Oh, a little safety tip here...
I have both a light and my iron plugged into the same power strip. I ALWAYS know if I've left my iron on when I leave my sewing room because the light is still on. Light off -- iron off; light on -- iron on.