Looked At Bikes Yesterday

For me, it was price. When I decided to start riding again some 18 months ago I was not ready to invest thousands, not knowing if I would stick with it. In 2008 I bought a 2006 model from my LBS, full Carbon with Ultegra group except brakes. The Scattante CFR served me well, although it is not problem free.
If I had to do it over again I would look for a smaller shop who carries brands I am interested in. Smaller, because I would want someone to spend time with me for a correct fit prior to buying the bicycle, and to remember me when I come back after the purchase. Quality components are key and money well spend, but I don’t need the top of the line. I can’t tell the difference between and Ultegra and a Dura Ace, but I know that the Ultegra is solid. My next bicycle will likely be in the 3K+ range (once I have a job again and can justify the expense). While you are looking I highly recommend to test ride some of the more expensive bikes, you will feel and understand why they cost more, but it will also help you in your decision what you want/need and what does not matter.

I should also point out that I don’t mind buying a bare frame, and building up the bike myself, which greatly influences how I buy bikes.

I bought a new road bike this year. Instead of setting a limit on price from the start, I looked for the bike I wanted, then tried to build it so it would be affordable for me. I determined that the difference between the Madone 6.9 and 6.5 were not much, so I went with the 6.5. I had it built up with Ultegra, and saved a lot of money over SRAM Red. I spent some money, for sure, but the difference in weight and ride quality were worth it. I figured that I knew going in that I love cycling, having logged tens of thousands of miles, and so I didn’t mind spending some money to get quality. I am a much faster cyclist with the Madone than I was before, especially on the climbs.
I agree Jeremy that the Ultegra is well worth it, but the Dura Ace is not.

As you move up from 105 to Ultegra to DA, you start seeing weight savings. But also, you find bearings instead of bushings, or better bearings, or shorter shift throws. Shifts get noticeably cleaner.
I’m very partial to Ultegra and cannot justify the DA tag, esp. for the parts that wear out — cassettes, chains, chainrings. It’s a racket.
Having said that, I’d add that unless you’re going to race or spend 10 hours a week on rolling terrain, odds are you’ll do just fine w/ 105.
When I first bought, I figured, pay for the better components — framesets are somewhat generic. I bought a decent steel bike w/ full Ultegra. But it was a shade too small, and it beat me up on longer rides because it was very stiff. (Steel is NOT inherently compliant, as the mythmakers will have you believe. It depends on geometry and build. Steel is a stiffer metal than aluminum.)
Then I got a carbon-fiber Bianchi 928 (mine’s no longer made). It’s 20% lighter, more compliant than my other bike and won’t rust. I’ve raced it and lost count of the wrecks. It is completely unfazed. (Another myth: Carbon breaks. Not very often — this is the 21st century, not the 20th.) Best part: I paid <$1,800 for it w/ Ultegra shift/brake levers, brakes and rear D; the rest was 105 except crappy, chain-dropping FSA crankset. (Note: I do know what a limit screw is. So does the best mechanic in town, and he couldn't get it to shift cleanly). Repl. that w/ Ultegra. Never a missed shift or dropped chain since, even under load.)
Now I believe the opposite of my earlier conclusion: Buy the best frame you can afford — carbon or ti — and try to get it w/ Ultegra 10 shift/brake levers (or Rival). Then upgrade the rest to Ultegra as parts wear out.

Bryan — you seem like a guy that wants to keep a bike for a long time. With that in mind, I suggest a high end steel frame. That will be my next bike, regardless of gruppo.