Originally Posted by
LGHT
Try and find a "beater" a bike that doesn't look cool and more importantly doesn't cost much, but works and rides. Then figure out if you even want to ride seriously or not. I know several guys who went out and spent $1k+ on new bikes only to realize it's a tough sport and they really didn't want to work that hard to get back into shape so the bike just sits in the garage for years until it ends up on Craigslist for less than half of what they paid for it. My first road bike was $125 and I rode that thing for a few hundred miles before deciding on upgrading.
I actually disagree - I think he's on the right track looking at serviceable well maintained road bikes with index shifting that cost $800-$1000 when new and are nowadays worth $300-400. That's good enough to keep and use if he likes riding, and also good enough but reasonably priced enough and sufficiently depreciated to not take a bath on if he ends up selling it. A cheap beater might discourage him and be more trouble than it's worth.