I'd seriously consider checking out what your local bike shops have to offer, especially in the way of used bikes. A good used bike - particularly one that is well maintained by your LBS - could offer you a lot more value for the money, and as others have said, you won't be heartbroken if it gets damaged or stolen.
A new bike shop in my town specializes in urban bicycles for commuting and just general riding, and they have a several, older Raleighs, etc. that they repair, restore, and clean up for resale. These never last too long. They are classic bikes, ride great, and because they don't look like the latest or greatest, are not as obvious targets for bike theft.
Unless you plan on moving up to "hardcore" riding or racing, my personal opinion is to not buy more bike than you think you can handle. I'm no mechanic, but I used to maintain my cheap, big box road bike when I was a kid. A pain, but easy to do. Since then, I've gotten more bikes, including a fat bike with "modern" components: thumb shifters, disc brakes, aluminum frame, etc. But technology creep can be deceptive, and the latest and greatest doesn't necessary benefit the ordinary person in normal riding conditions. And under most riding conditions, the difference between say, 8 gears and 9 gears, is pretty insignificant. But I like my Rivendell bikes - nice and simple technology, clean lines, easy to maintain. And don't be fooled: some of the older bikes can go pretty bloody fast too! Your mileage might vary, of course.
Good luck with your decision!