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Welcome Back!
The NSAS (Northern Sydney Astronomical Society) have viewing nights regularly(?) at the Turramurra Golf Course...
I'd encourage you to contact them and get out and see a few scopes before you buy...I'm in East Lindfield and would be happy to show you my gear once I get it all unpacked (we just moved into a new house)...
There is also a group from this site that meet monthly (or so) up at Kulunura (towards Gosford from Sydney)...usually a few different types of scopes are there and there is pretty good company and the hedgehogs (smoked or not) are outstanding!
To try and answer your questions...
#1 You could sell it here...and yes, just like a new car once a telescope leaves the shop it declines in value...
#2 at "normal" magnification it is not difficult to track (by hand) an object in a well set up Dobsonian...it does take a bit of practice but it is not difficult.
Clear Skies!
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