For what it's worth, here is my advice:
Use your 9.25" SCT for the moon and planets...........and use your 100mm for deep sky. The 9.25" has a very long focal length......your field of view will be too small for most deep sky objects. Conversely, the long focal length will be an advantage for solar system imaging......where you want to be up close and personal with the planets....they are tiny targets.
Use the shorter focal length 100mm for deep sky....to give you a much wider field of view. A wider field of view will also reduce the effect of tracking errors.
Your DSLR will make a great deep sky camera. NOTHING you can buy for anywhere near the same price will produce images as good! Meade DSI's and Orion StarShoots are great guide cameras, but they will not come close to a DSLR in image quality!
You can certainly go for a high-end CCD, if the budget will allow, but a DSLR is VERY hard to beat.
The secret of astro-photography (deep sky and solar system) is aligning and stacking multiple exposures! Even the Hubble Space Telescope uses this method. With a webcam, you are going to capture an approximate 1-3 minute video clip......about 2000 frames give or take. With your DSLR, you are going to capture multiple exposures (depends on your tracking accuracy) of 15 to 300 seconds each. The more the better, generally. In both cases, software then aligns and stacks the individual frames to create a single image.