Hi Sean. There are lots of suggestions being offered here which is great. My advice is is to go with a setup that is easy to use, that will minimise your setup time and frustration, and maximise imaging time - and at a reasonable price.
For a camera, I reckon it will be much easier to learn with a DSLR, than getting straight into a astro CCD, and also much much cheaper. Look at
Justin Tilbrook's photos in the Deep Space section. He is using an un-modded Canon 1100D and getting some great results, and that camera can be purchased for less than $400.
For a 'scope', you again want something that is easy to handle and quick to setup. Newtonians give lots of aperture at a cheap price, but need good collimation to produce the goods. I started with a 200mm f4 newtonian, which is affordable and can produce nice shots, but can also be very time consuming to collimate well - just what you don't want when you only have a few hours available each evening to take photos. A better option might be an
Skywatcher ED80. No collimation required. Just attach the
field flattener and your camera and off you go. jjjnettie on the IIS forums has had her photos taken with an ED80 and DSLR displayed at the NASA Goddard Institute, so you certainly can get good results with this gear.
Camera lenses are an even cheaper option. I actually shot a lot of my images last year with camera lenses instead of my newtonian. Lenses are very affordable, quick to setup, don't require a field flatenenr, and are nice and light weight meaning that its less demanding on the mount. I also use a DSLR for my images. See here (images grouped under "Nikkor and "Rubinar" are taken with camera lenses):
http://www.astrobin.com/users/rmuhlack/?public&sub=gear
For a mount, I reckon that a GOTO eq mount is really a must, because it just makes finding the objects you want to shoot *so much faster and easier*. A GOTO mount also will make it much faster to polar align, because you can use the polar alignment tools on the mount to get you aligned quickly. GOTO mounts can also be controlled by a laptop, which makes it even more versatile. Your have limited time available to take astrophotos like we all do, (like on a weekday, or if there is clouds approaching) I'd rather as little time as possible setting up so I can spend as much time as possible actually taking photos.
If you're only using camera lenses, you could get away with a light weight mount like an EQ3 GOTO, however if you're using a telescope, then a HEQ5 is probably a safer bet. In the IIS classifieds, there are currently a couple of HEQ5 mounts for sale for $900, just to give an idea of the second hand price.
Sorry for the long post. Hopefully that gives you a few more ideas to consider