500 feet in two miles is not a case of any bike will work, for a new commuter. I couldn't do it on my fixed gear bike for example, and it wouldn't be a piece of cake on my road bike either. You need to find something that is geared for climbs. Probably a hybrid with mtb gearing, or a mountain bike of course.

If you do want to go with a road bike look for something with a triple chainring or at least a compact double, and with big cogs in back.

I do not advise budgeting a significant amount for accessories - put it on a better bike and buy better accessories as and if you decide you need them. $20 for front light, $10 for back and you're set. I have a $13 rack from Amazon that's fine for me, but you might not even need that. It's better to have the bike that you'll ride, and you can always pick up the nice-to-have's later.