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Hi Josh,
the thing about telescope choice is that there is no right answer. Every scope is a balance of features and ambitions on the one hand with cost on the other.
You have a dob that sounds pretty portable. I strongly suggest you make contact with either your closest astro club or other astronomers in your area and spend time with them. Take your scope to a few club functions, see what others are doing, have a look through other scopes, get a sense of what is possible and what isn't. Don't spend your hard-earned cash yet. Instead, get yourself some time under dark skies with other astronomers and their scopes.
After a while, the answer to your question will become much simpler as your knowledge and interest grows.
Peter
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