I've only recently got back into astronomy ... and I'm a long way from having any sort of expertise ... so take the following as possibly lacking the credibility of our more experienced members.
I found
THIS thread quite helpful in deciding which way to go.
I ended up buying a second-hand (from the IIS classifieds) basic 8" dob (not the goto version) and I'm extremely happy with it. I've found it easy to come to grips with and slowly but surely I'm learning my way around the sky.
I also had a yearning to play with astrophotography but came to the same conclusion as you in as much as I realised a significant budget would be required for significant results.
Instead I bought a small (90mm), inexpensive Mak on a basic alt/az goto mount second hand from Ebay as well as the little Celestron NexImage webcam. This combination has yielded a lot of fun and has the advantage that the whole setup is very portable and goes away camping with me on many weekends.
The entire spend was under $700.
I have subsequently bought some additional eyepieces. I don't mind spending a bit on these as I figure they'll stay with me even if the 'scopes are upgraded. Like you I have a fair bit of normal photography gear so it's a bit like buying premium lenses ... they'll last a lifetime even though the camera bodies might come and go.
... Oh ... and welcome, from one newbie to another.
