Hi BC and Welcome to the Group,
I tend to agree with Geoff and Phil. I have owned both dobsonians and equatorially mounted scopes over many years and for visual observing much prefer a dob. If you want to take "top class" astrophotos then you need a tracking mount.
Given that your skies are good you are better off going for as much aperture as you can afford and given your budget, decent aperture will only come on a dobsonian mount. However just because dob mounts are cheap they aren't crappy, they are in fact more solid and vibration free than "most" equatorial mounts (some exceptions), as you correctly point out what they lack is the ability to track motorised in there simple format.
Don't be put off by faster F-Ratio scopes, anything slower than F5 is manageable for a beginner in terms of collimation and eyepieces, however there will be compromises. eg. $80 widefield eyepieces won't work well at F5 but they dont work well at F6 either so this shouldn't be a consideration. There are any number of top quality medium cost eyepieces that perform exceptionally well at F5 eg Uo orthos, Celestron Ultimas and televue Plossls all cost under $150 and provide superb image quality in an F5 scope. The downside of these eyepieces is a narrower FOV and short eye relief.
You are placing a major emphasis on difficulty tracking with a dob. You shouldn't its not hard, I can track with my 10" dob at over 500X on planets and my 8 yr old can track at 300X with it. What it takes is a little bit of practice and I mean a little bit, not a lot. Given lots of experience you can almost track with a dob like its a driven mount. I can have Jupiter in the FOV at 250X, leave the scope stationary for several minutes, come back to the scope and pull it straight back into the FOV without the finder 9/10 times (because I know where its moving) this comes with experience but there is nothing difficult with using a dob from day one. A dob can also be fitted easily with DSC's which are computerised aid in finding objects very easily.
I think you would be well served with a 10"/f5 GSO dob and you would have money left for some necessary accessories, like star charts a couple of good books, a planisphere and a red torch.
I suggest you take Strings advice and attend some star parties and spend some time using different types and sizes of scopes to see what you like to look through. Then I think you should attend the next star party and take careful note of all the guys "frigging around wasting precious time and experiencing all sorts of hassles" setting up their equatorially mounted scopes compared to how long it takes the guys to set up there 10" dobs. You will find the guys with 10" dobs start observing 20 minutes before the guys with eq mounts and when it comes time to pack up you will find the guys with 10" dobs home in bed asleep while the eq mount guys are still frigging around folding up their tripod legs.
I think eq mounts are great but they are definately more suited to a permanent observatory situation IMO. A medium sized dob in the 8" to 12" class is certainly a LOT more portable and convenient than an 8" eq mounted newt IMO.
BTW my advice is free and worth every penny
CS-John B