(there are actually questions bellow my story here, to skip to them go to the bold text if you're feeling lazy)

So I JUST bought a brand new Specialized Sirrus sport about 4 months ago, i do love it, but i feel like i'm already starting to outgrow it. Having not ridden for about 8 years I figured I'd end up just doing 10-15 mile rides for exercise but not much more than that. Well turns out I was wrong. I'm consistently doing a minimum of 20 miles/ride now and looking to do a 50 mile ride in about a month. The thing is on some of the longer rides the bike just doesn't give the extra hand positions or aerodynamics that I'm starting to want.

Now, there really was no way for me to anticipate this would happen so I don't regret buying the bike per se, but I'm having a hard time rationalizing trying to sell a 4 month old bike just to go out and buy another bike.

Questions
1. Am I dumb for wanting to sell a 4 month old hyrbrid to get a road bike
2. Any advice on how much I could ask for a 4 month of Specialized Sirrus Sport? It's in perfect shape. Also any advice on where to sell it?

3. Any advice on bikes to look at? I'm still a very big guy though losing weight from riding (6 ft 285) , I test rode an Alez Elite (geometry felt a bike too aggressive to me) and a Cannondale Caad 9 6 (felt FAST, though I had a bit of worry that the bike felt too stiff, felt like everything from the pavement transmitted right through the seat/bars, worried that could become tiring over a long ride but hard to tell over a quick test ride.) What else should I consider in similar price range $1000-$1100

This is sort of a lot of questions but you guys haven't steered me wrong yet.