Hi confined.
Welcome to astronomy, the hobby/interest that will be around as long as we have space up there!
As far as buying now and updating later, that is a great idea. Around December Andrews will have their new 16" Dob available. Buy one and when you are ready to upgrade to GoTo I will buy the 16" off you for about $300. It will be used by then and second hand scopes aren't worth much as the beams from from your eyes wear the mirror out!
Oh, you will also need Nagler eyepieces for that 16", but don't worry, I'll grab those off you to when you sell me the scope. $20 each should cover it.
I think Ving will want your series 500 eyepieces though! Just give them to him
Confined, please ignore all the above dribble and welcome aboard