Hi Pete,
An 8" goto synscan Skywatcher Dobsonian will set you back $999 at
Andrews Communications and this will be PERFECT to get you started, for the following reasons....
1) It is one of the simplest and easiest scopes to set up and use.
2) Very portable so you can take it out the back or in the car to get to a dark sky site away from city lights.
3) Big enough to be able to see galaxies and globular clusters with amazing details
4) Having goto and tracking means you can "dial up" an object and the system will drive the scope to it and then track it for HOURS without it moving in the eyepiece. This is especially handy when looking at high magnification at a galaxy or planet.
5) using a webcam or one shot camera / DSLR through the focuser allows pics of the moon, planets and some Deep sky objects without breaking the bank.
6) 99% of people here on IIS will probably recommend an 8" dob as it is perfect bang for your buck to get you going.
Of course, you could get a larger dob for less money than the 8" goto version, however, without the motors and the computer handset to drive it, you will be having to nudge the dob constantly at high magnification which gets frustrating quite quickly.
Now at $999, you pretty much have blown all your budget, however, with this scope and nothing else (except say a laser collimator for about $70) you are likely to be able to do all the things you mentioned straight away, and this scope is one you should keep for a LOOOONG time.
You will no doubt be tempted with going for the 10" or 12" goto or non goto variants, but really, these should be kept for say 2-3 years down the track when you have exhausted the potential of the 8". Like we all say, it won't be your first scope unless you lose interest and if you get too big a scope now, you may not use it as much as the 8" and therefore more likely to stay inside rather than take it out and use it.
The scope that gets used the most is the best scope in the world. My opinion is that the 8" goto collapsible dobsonian is the best choice for under $1000 for the reasons I mentioned above.
I have a 8" tube on an HEQ5 pro which pretty much replaced my need for the 12" dobsonian I had, so i ended up selling the 12" as I was amazed at how well the 8" views compared to the 12" and because of the tracking and goto of the mount, sated my geek factor within also.
Hope this helps.
Cheers
Chris