well heres my 2cents
i would head back to the specialized dealer and take a few bikes on test rides
get a feel for the difference between the $500 component groups and the $1000 groups, try steel vs. al. vs. carbon frames
try a few different brands and lines between brands, they all have slightly different geometries catering to different body and riding types, some will just plain feel better than others, take note of this

now that you have a few miles and bikes under your belt, make a decision, pick a few brands you liked, the correct size you need, the component brand you are looking for and do some used searching
craigslist is great, i got both my bikes off the OR classified newspapers, before cl's time
expect to pay about half price for a 4-5 yr old decent bike, by decent i mean over $1k new

things to watch for
good wheels make a good bike, they are important and expensive, lighterweight well built wheels show up on some brands in the 1k range but not others, dont let this be the cheaped out option on the bike
shifters and deraillers are pretty decent these days, top of the line are great but mid grade is just fine
fingertip shifters>>>>downtube
invest in riding shorts, spandex is amazing and your balls will thank you on anything over 20 miles
clipless pedals>>>>toeclips, the scrapes on your knees will be a badge of honor

there are so many brands out there just focus on finding a well fitting bike and one that has the level of quality you want
focus on shoulder and back comfort, steering feel(light flighty, or to slow), wrist comfort
make them move the seat forward a bit and let you ride it around, then back a bit and ride it around up a bit and ride, down a bit and ride
every suptle adjustment will change the feel, so watch these changes and look for what feels best for you
make the shop techs show you exactly how to check size and fitment of the frame also, so you can test yourself when looking used

find a $500 used road bike, try it out this spring and summer, get a few 30+ rides in and see if you like it, then you can upgrade your bike and make it pretty damn nice with your decent starting platform
if you dont like riding all that much, the bike will last you the rest of your life as a nice bike that you occasionaly use, not a bad investment imo

im all for used, and all for quality, bikes are something everyone should have and enjoy imo