sub $1000 is not the best budget - with that budget you'll get way more comfort for you money buying used if you can do the necessary research so that you make the right decision when it comes to getting a bike that's the right size and fits you well.

i'm another big advocate of steel frames. i think the Jamis Quest would be a good choice - with the stem turned up if the angle puts too much weight on your wrists at first. it'll run $1300 new but it's a sensible mix of quality stuff at a price that isn't affected by the brand name. you can only get cheap alum or mixed material bikes new for under a grand (stinks but it's true) and these won't be as comfortable as a nice steel frame.

this summer i helped four different people get new bikes. 3 out of 4 got steel and 3 out of four used eBay and all are pretty well satisfied. the reason for not buying from an LBS was always the same: not comfortable spending over $1k for a first road bike and the ones for under that were poorer quality and less comfortable compared to what they ended up with shopping online.

but while you can get a bunch of great choices used - like on eBay or craigslist - this requires that you put your time in test riding bikes so that you can learn for sure which size fits you best in which brands. i will typically illicit one reponse to the tune of "you jerk, you shouldn't use those poor LBS people for test rides and then not buy there!" but as you'll recall these were all friends of mine i was helping and it's not like i wanted to see them on a cheap alum frame with a Sora group for $800+tax and it's not like they were trying to spend $1500 to get a Bianchi Vigorelli or even $1250 for a Bianchi Imola. This reinforces my point by the way - those bikes are comfortably out of reach of somebody thinking "under a grand" and that's practically everybody when it comes to first-timers. another good choice in the $1200 range is the Lemond Croix de Fer.

lastly, become aware that top tube length is important. make a list of how long the TT is on the bikes you ride and how it felt to you when properly fitted. and notice if the bikes you're riding are measured center-to-center (c-c) or center-to-top (c-t) as this makes for a 1cm or so difference.

oh, and consider getting a triple if you live near any significant hills - esp if you have joint trouble.

good luck!