I had my Dragonfly built up with 2006 Record carbon compact 50-34 crank and the 13-29 cassette (I loves the hills). I don't find the jump from 34 -> 50 a problem at all. That said I've never ridden a "standard" double crankset. I went from std. triple to FSA 50-34 compact to this bike with the record compact. I don't know how well a 53-39 shifts so I don't feel like I'm missing out.
One thing that I didn't like about my setup was spinning out the 50-13 gear around 36mph on a descent. I swapped the 13T for a 12T myself with no problem. It gave me a few more MPH but I still spin it out once in a while on fast descents. I'm hesitant to try replacing the 12T with an 11T. Does anyone know if that can even be done?
As for your issue, the cassette & derailleur swap would be the easiest and cheapest thing to do, and I'd agree with most posters that the main difference you'll notice with 2007 UT record is the price.