Hey, LTD—
I started on exactly the same hybrid you have, and I still have great affection for that bike because it was the one that got me into cycling. I rode it for about eight months before I got the fever for a road bike, and I've never looked back. (I finally sold the hybrid last year because I knew it was bored hanging in my garage and ready to spark someone new into cycling.)
If you're doing flat distance rides, aren't much interested in upping your average speed, and like the upright riding position, there's not a ton of incentive to upgrade—bike store road bikes tend to start at around $700 and go up from there, so it's not an insignificant investment.
On the other hand, it sounds like you've made very significant investments in yourself in terms of weight loss and energy gains, and if you'd like to continue to "grow" as a cyclist, road bikes can help you do just that, particularly in terms of speed and climbing abilities. Of course, if you do expect to ride with your DH on your road bike (assuming he doesn't invest in a new bike), you may have to gear down so that he can keep up with you! Hee hee.
Here's the "learn from my mistake" section. I bought my first road bike on eBay and saved $1,000 off the retail price. But the savings weren't worth it in the end, because as much as I tried to measure myself and figure out what I needed, the bike I bought was never quite right. After several tweaks in desperate attempts to make it work, I finally bought a new bike this year—at full retail—and I'm much happier for the investment.
We're all individuals, and road bikes, more than any other type, must be fitted correctly. Because of the way the riding style distributes weight and pressure (whereas on upright bikes, your butt bears most of the pressure), getting the balance right is crucial to avoid discomfort or even injury, particularly in the neck, shoulders, and back. When you buy from a reputable bike store, they'll fit you correctly, sometimes swapping out stock parts gratis to accommodate your body. You'll ride happier and longer as a result. (And you can still save some bucks off the retail price in your local bike shop if you don't mind buying last year's model.)
Congratulations on your accomplishments so far, and good luck in future riding, whether you decide to make the switch or stick to your trusty steed.



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