Sounds like you have way too many requirements, and too large of a budget for a first setup. The higher your expectations and the higher your initial expenditure, the more potential there will be for getting into something that may not be right for you.
First off, forget astrophotography, even if you're already good with photography. That will make your decision a LOT easier and reduce your almost guaranteed frustration...
(1) If you have little or no observing experience, I suggest either borrowing or spending the $150 on a good pair of binoculars (10x50 or similar), and borrowing/buying some good beginning observing books and basic star atlases from the local library (preferrably ones that don't get you obsessing over equipment) like Turn Left at Orion, Binocular Astronomy, Norton's Star Atlas, The Cambridge Star Atlas, etc. This way you've spent very little to discover if the subtle enjoyments of astronomy is for you. And when you do step up to a "real" scope, you'll appreciate it more, and will find navigating the skies a lot easier!
(2) If you have a little more observing experience or are really ambitious or impatient, then by all means go get a scope. But get a EASY non-computerized one like a 6" to 10" dobsonian (Orion XT8 is perfect - Only $349. And if this scope can't make you happy for at least a few months, I'll speculate that nothing can...)
(3) ... and if after a year of visual observing with your 6" - 8" dob, you're still having fun and excited about astronomy, then you can consider astrophotography desires...
I love astronomy and I love photography, but I have never started astrophotograhy. Maybe I never will...
I used to be REALLY BIG into photography once. Back then, in my photographic pursuits, I used to wonder why other people did't see or appreciate moments like I did. Its "magic light" hour, and all my friends are just sitting around. I would run around to find the best vantage points and find the best scenes to photograph and wait for the "perfect" light. I had to capture the "best" pictures. ... Later on, after my obsessions subsided, looking back, I think I missed fully appreciating the moments also - too much time and energy and focus on capturing the picture just right and letting the moment pass by without really fully appreciating it (not capturing it)...
Astronomy takes a lot more patience to appreciate (and much worst photograph) then dramatic sunsets, grand landscapes, violent weather, or even subtle patterns in closeup photography...
... Be patient. Don't jump in. Learn to appreciate first....