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Hi Matt,
and welcome to IIS!
there is a saying: the best telescope is the one use the most.
And a 5" Newton is not bad for a start.
As for astrophotography, I would recommend to a DSLR, a wide angle lens and a motor for the right ascension axis of your telescope (east-west) then get an adaptor to mount your camera on a dovetail, pol align your mount and take lots of 30sec exposures of the Milky Way. Stack them with the free deepsky stacker (google DSS) adjust contrast, brightness, saturation and see if you like that. Do it from way out of town on a moonless night or else it'll be too bright for that.
If you like what you get and you want more than you need to be prepared to fork out a few grand.
AP is a dark art and a very expemsive one too.
Clear Skies!
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