I have done a fair bit of astrophotography, and I hope I can offer some insight, too.
I think the astro-CCD vs. a DSLR can really go either way: it all depends on what you want to do really.
IF you want to end up doing actual research with your setup, an astro-CCD is the way to go. DSLR research can be done, but the bayer matrix in front of the sensor greatly increases your workload to get useful data out of it. One has a lot more work and planning to get a good colour astro-CCD shot . . . since one must take separate photographs for R, G, and B to get colour. There are some full colour astro-CCD's out there, but do the research before buying it. Those will need power from significant batteries vs. what you need for a DSLR.
For just pretty photographs, I would honestly say a modern DSLR can be not only a good choice, but a great one. More than one company will modify DSLR cameras to completely remove the IR filter, or replace it with one that allows a LOT more of the deep red hydrogen alpha light to reach the sensor. At least one company also modifies the DSLR's to include a cold finger under the sensor which GREATLY reduces overall noise.
http://www.centralds.net for more information if you care to go that route. Post processing can be half the battle, and there are lots of good software packages dedicated just to astrophotography.
That said, you can do amazingly good work with just a DSLR and lens on an equatorial mount that will track the sky.
As an example, this shot is straight from my camera (which has NOT been modified, btw) . . . meaning no dark frame reduction (LENR was OFF), no colour corrections, and no levels adjustment: just a resize and a conversion to JPEG. This is the full frame using a 200mm lens. I think I can get a result I'm really proud of with some processing . . . but I'm pretty happy to start with since this is straight from the camera!
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Your 500mm lens will work on a tracking mount as long as the mount can handle the weight. The better the mount, the more wind you will also be able to deal with before it becomes an problem, too. I would advise starting out with wide angle to low telephoto lenses as you learn how to properly align a tracking mount. The longer the focal length, the more apparent tracking error will be.
Hope this adds something helpful to your thoughts.