Not sure what gearing you have on your T800s. IIRC Cannondale played around with the gearing a bit over the years.
The cassette in the rear is (relatively) cheap and easy to change, if you don't have at least a 32 in back. Changing the crank is a bit more difficult and expensive, but if you don't already have a 26 or smaller chainring, the crank can be changed for something smaller. If your front derailer can handle it, go for a 24 or even 22 small ring. (Front derailers are sometimes a bit fiddly to set up.) I'd guess your LBS can set you up for $250, worst case.
If you do have a bad case of new-bikeitis, this year's Randonnees have gone to 10 speed. Unfortunate, since replacement parts will be more expensive. OTOH, they've got nice gearing. LHT is pretty similar as far as frame and weight, and still has the less expensive 9-speed setup. Either will work, I'd call it a toss-up.