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Hi Craig and Welcome! Most people learn how to track with a dobsonian-mounted reflector at high magnifications - IF the bearings are good. Most of the commercial ones don't come with the best bearings and can be a bit difficult and jerky. Some simple attention to them - cleaning and applying silicone polish to the laminate/plastic surfaces that the teflon bearings touch can help. Better is to put in a better laminate surface ("Ebony Star") and better teflon (advice is in the threads on this site). If you are a do-it-yourself type of person, this is all straightforward. I did this and had a newbie successfully track Jupiter at several hundred magnification.
Then for a relatively small amount of money compared to your budget, you will get a great reflecting telescope with great light gathering capability (8" or 10", say). Then you can spend the rest of the money on a couple of good (several hundred dollars) eyepieces to make your observing super. The next step to save for is about $1,000 to install computerised pointing (eg. ArgoNavis system) to take the effort out of finding things in your eyepiece. The only thing missing is motorised goto (who needs that - Sheesh!) and motorised tracking (yes, nice to have), but there is an option. About $1,000 gets you an equatorial platform on which you can place the dobsonian mount and you will get 30-40 minutes of tracking of objects.
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