Like Chase said, you can expect to go through 3-4 shelters as you refine your goals and build up your lightweight kit. In fact, that's about where I'm at now.
My first (non-lightweight) shelter was a Sierra Designs Flashlight Clip, which I really enjoyed and took on a number of (mostly car-) camping trips. But after hauling it and the rest of my gear up from the Colorado in the Grand Canyon, I decided it was time to go lighter.
My first truly lightweight shelter was a TarpTent Rainbow, which I still own and use. However, it's mostly been relegated to two-person use. It's a bit tight, but it works plenty well if you're comfortable with the other person. My wife won't sleep in a floorless shelter, and she likes to be close, so it's worked reasonably well for us. At some point, I'd like to replace it with a StratoSpire 2, but we're happy for now and the money is better spent elsewhere. The Rainbow is light enough that if I take it out for solo use--especially when the bugs are out--I don't feel penalized for it. I just don't do that much anymore.
My third shelter is a silnylon tarp that I made myself. As a shaped tarp, it doesn't have too many options in pitching, and it's actually rather simple to set up now that I have the hang of it. I'm pleased with it overall, and it's light and airy, all good things in the summer. But as it was my first real MYOG project, there are a lot of things I would do differently if I made it again. I think I've accounted for all my mistakes (time will tell), but there's a perfectionist in me that wants to make it better and a little differently.
My fourth shelter isn't technically my fourth shelter yet. I ordered a Duomid about three weeks ago, and I'm waiting for Ron to make it and send it my way. My reasoning behind the Duomid is that I want something that can handle any weather I care to be out in. I'm very interested in expanding my skills to winter camping, but I don't have a proper shelter for that yet. Given the Duomid's ability to handle wind, rain, snow, or most anything else (except griz), I have had my eye on this shelter for a year and a half now. So, I can't say for sure that I'll like it, but after a lot of research and contemplation, I think it will fit my needs nicely. I'm hoping that once I get it and set it all up, my wife will decide that she's okay with going floorless, and she can use it with me. It might be a tight fight for two in nasty weather, but that's how we like it anyway.
I'm also planning on making a flat, probably square, tarp sometime in the next few months. If I make it out of silnylon, it will only cost $60 or so in materials, and I've been itching to apply what I learned from my first tarp on another project. RJ's recent article got me thinking that this could be a fun thing to sew when I get some free time in April-May. The weight would only be slightly less than the Duomid, but the creativity in pitching options would be a lot of fun to play around with. I also haven't worked on my knot-tying skills since rock-climbing in college nearly a decade ago, so that's a serious advantage too.
Honestly, I'm hoping that these last two will be my only new shelters for a long while. I don't like to have too much gear, and this list is already long.
I also don't see the value in cuben fiber. For me, the cost per ounce of upgrading to cuben shelters is around $20/oz. That's more than I'm willing to pay, and I'd rather put the money elsewhere, into something like packrafting. Plenty around here disagree, and if I could afford cuben, honestly, I'd probably go for it. Right now, though, the tradeoffs are too high as that limits my expansion into other areas of wilderness travel.
So there you have it. I hope it helps you make some decisions. Of course, everyone's choice is always deeply contextual, but in seeing why some make the decisions they do, you can get a good idea of what you're experience might be.
/*/Edited: damn you grammar and spelling/*/