I'm about a year downriver from you. Here is what I did.

I shopped around for a dealer who really cared for me as a person and as a customer. I followed his recommendation. After riding several of his bikes I followed his recommendatioin to buy a hybrid. It cost nearly twice what you say you want to spend and the price just about gave me a heart attack. But, it was very nice to ride. Because it was nice to ride I rode a lot.

Second season, this year, I found that I really wanted to ride roads. The hybrid just wouldn't do that as well as I wanted. So, back to the LBS. Again I rode bikes until I found one that met the primary criteria: Comfort. I ride a lot on rough, rough roads with cracked pavement, loose gravel and potholes. Comfort!! I ended up again with a bike that was way more expensive than I wanted to spend. But, it is full carbon and is very comfortable, climbs the hills very well and can crank out the miles with little effort. This time the price only caused a few palpitations. I love the bike. I can crank out distance and hills and enjoy it.

For a road bike there simply is no substitute for a modern full carbon bike if you want comfort. Other materials are cheaper and have other redeeming values. But, modern carbon bikes have flex built in that dampens road shock while at the same time being very stiff where they need to be.

Now I have two bikes that fill all my needs. I've got Way More money in them than I wanted. But, they are comfortable, perform very well and are durable. Plus, when I get ready to sell either or both there will be relatively more residual value than cheaper bikes.

Oh, why no used bike? Simple, when starting out I didn't know enough to make a good deal. Now I do; which is why I bought another(3rd) bike off Craigs List a couple months ago.