Originally Posted by Standalone

This is my usual advice: go to the "Classic and Vintage" forum. Ask around. Buy a decent old bike that is in good shape from CL. Become fast, efficient and safe on an said old school road bike. Then buy a more serious road bike-- one that your own experience will help you choose. Put fenders on the old one and ride it to work/in the rain/shopping/the bar/etc.

Worked for me-- I turned in a 6 hour hilly century before really considering anything modern. And now, on a more modern bike (still only $350 used) I'm more mentally toughened up by being habituated to DT shifting 12 speeds, and believe that I am a better rider for it.

The other bonus is that, with the upgrades/tuneup to the old road bike, your budget can be spent on a local CL seller, local bike shop, etc. Rather than sending $1000 "direct"ly to Taiwan.