Been there. You start out reading on the internet about how somebody got a mint Bianchi for $250 and somebody else found a LeMond for $300 but when you look at CL all you see is clapped-out Motobecanes for $275. If a $300 Klein shows up it's gone by the time you call. Everybody is different in what they consider to be satisfactory. I won't spend money I don't have and I try to avoid unwise purchases, but once the money has changed hands that's the end of it for me, I won't lose sleep over what I paid and I won't compare myself to the guy who found the same bike in a dumpster after an estate sale. Losing any appreciable amount of riding because a bike was priced $100 higher than the internet said doesn't strike me as a great deal, especially if your rebound move is to buy a bike from Wal-Mart. But you're the one to live with the hole in your wallet.

For reference, I bought a last-year's aluminum Jamis for my wife from a LBS for $600, MSRP was $8-something. Road bikes are a couple hundred more than entry level in other categories. But I still would give LBSes a chance. If nothing else, the test rides may help you with your uncertainty about whether you'll enjoy it or not. You may find that you'd be happy on a hybrid or a city bike, which would save some money new or open up your search options a bit on CL. In the end, unless it's a matter of paying your bills or not, it doesn't whether you spend $300 or $450 on a bike, it matters whether if fits you and you will ride it and improve your health and life.