300 is not going to get you into a road bike at all unless it is used or off craigslist which is okay or can be better anyways. you can get a decent hybid or mountain bike with 300 but for a road bike your gonna want to at least HAVE some more money even if you find the prize and don't have to spend it all.

Any good Entry level road bike would be great for anyone who is actually interested. A bike like a Specialized Allez, Giant Defy, Trek 1.x, even a Caad 9, are all great choices for getting somebody in the saddle and having them stay there. It is easy to spend 500 dollars and not like your ride and never ride because of it. it is just as easy to spend 500 and realize what you've been missing all this time and you get your money's worth in 2 weeks worth of riding.

Test rid everything before you bu anything and pick out the one your dream about. Enjoy the ride.

Flat bar options would be the Giant FCR, Specialized Globe, Diamondback Insight, or the Fuji.