Hi Paul,
As a 2-year newbie to the astrophotography side of things, I can pass on a few of my experiences. Of course, YMMV.
1 - Going the used route can save heaps of cash and as long as you do your homework first and are prepared to search around, you should be able to get a good goto imaging setup for well under $2K if you already have a camera. These items seldom get abused. I bought all my present scopes off the astronomy forums and have sold a few, too. BTW, what sort of camera do you have?
2 - Canon DSLR's are the best bet, it's the astro hobby standard and interfaces well to a laptop PC for total control. Very satisfying way to do things. A used 1000d or 450d would be a good starting point, although no doubt others will recommend the higher grade models. Only drawback with DSLR's is lack of cooling, meaning more potentially noisier pics, but they do a good job. I had a 1000d and it was excellent for my newbie needs.
3 - I'd definitely go the goto mount, makes imaging so much easier. Also look for used ones. They're relatively easy to maintain and repair, so don't be scared. EQ6/HEQ5/EQ5 in order of preference. Definitely no EQ3's or 4's (too small) and no Az/Els, they have movement limitations. If you can pick up a used HEQ5 at a good price, go for it. BTW, plenty of free software around (EQMOD, etc) to drive these mounts and cameras remotely from your PC.
3 - Scope? They're like cameras and have an f ratio, so faster scopes are more sensitive, all things being equal. Of course aperture size also matters a lot. a 4" scope just doesn't capture as many photons as a 10" one. Focal length is just like camera lenses too. You need shorter ones for wider sky views, and really long ones for the galaxies, etc. The Goldilocks conundrum

Oh, and long focal length introduces much tighter mechanical stability needs for long exposures.
So - The tradeoffs? Newtonian reflectors: Fast (f5/f6) and reasonably long >1000mm focal length, but big and clumsy.
Schmidt Cassegrain (SC) folded-type reflectors: Slower (f10), much longer focal length (2000mm) and compact. Some types can be easily changed over to fast (f2) widefield (400mm) functions as well)
Refractors : The Goldilocks solution

Not too slow (~f7), not too long (800-1200mm), not too big. And can give great pics.
I have finished up with one each of the above

Starter recommendation for DSLR imaging? Put your money into a good goto, preferably a used HEQ5, and get either a used 8" SC or reasonable 80-100mm aperture refractor. The Skywatcher ED80 is quite popular. Either will keep you happy on planets and brighter DSO's and will be readily saleable later if you want to upgrade.
Bolting a DSLR to any of them simply takes a $20 T-adaptor for the model of camera you have. (That's why standardising on a Canon makes it easier
As Marc says, get a dob if you want to do observing. Not my cup of tea, eyes too old and dim.
Drop me a PM if you want to natter further about things, including the going prices for used items. And no, I'm not a used equipment dealer
Cheers,