There really isn't a "cheap" dob and a "good quality" dob in our market. All the dobs you buy from the shops are good value, and come from 1 of 2 manufacturers (GSO or Synta).
Yes you can spend MORE on a dob, but that usually means the retailer is not discounting, NOT that you're getting a better quality product. A "good quality" dob usually means a custom-made truss dob with a premium mirror. That's much more than your $1500 budget.
So i'd discount your option 2 above as well.
If you want to get into photography, your budget will be blown straight away.
If you don't know how much you'll use it, stick with the dob to start out with - although make sure you understand how to find the objects, how to collimate, etc. If you don't use it much, and when you do try to use it you can't find anything interesting to look at, or the views are fuzzy/blurry because you haven't collimated, then you'll think you bought a dud or that astronomy is not the hobby for you.
The dobs come in sizes from 6" up to 16" (sometime next year). At the moment the best ready available sizes are 8", 10" and 12". Each have their pros and cons, in portability, aperture, cost, etc.
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