First get into astronomy, then astrophotography (Score 2, Informative)

My advice - learn the sky first. There's tons to see, and you'll need practice finding it. If you've been interested in astronomy, maybe you already have used binoculars (which is a good start) to scan the sky. If you're in a hurry and want to get your first telescope, I'll give the advice that was given to me -- get a Dobsonian reflector. Dobs are very easy to set up, don't require alignment, and are generally lighter (important if you're planning on carrying your scope). The downside is that you have to manually track what you're looking at, and simply can't do astrophotography. As many people have said, you'll have a hard time getting a good telescope with a good mount with a drive system for under $1000. What you can do is spend ~$500 on something like the Orion SkyQuest XT8 Intelliscope (that's what I have and I love it), use it for a while (maybe a couple years depending on how frequently you take it out) and get to know the night sky, then when you've saved up that $1000 again in your astronomy budget, get a nice equatorial mount for it with a drive system, put some rings on the tube and attach it to the mount instead of the Dobs base. Oh, and order a Barlow lens along with the scope. Also, I really enjoy having a solar filter - why limit your telescope to night use??

The time you spend learning the sky with your Dobs will also help you decide if you want to spend the extra money for the fancy mount, camera, etc.

One thing I'll point out that may be blindingly obvious to some, but comes as a surprise to others... for the most part, images in your telescope appear in black-and-white to the naked eye. There simply isn't enough light for your eye to detect color. Once you get a spiffy camera and that fancy mount, the longer exposure pictures will get you all the color you want.