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Hi Aaron.
An 8" dob is a great starting point or as an upgrade from a 5". Personally the so;id tube is not so difficult to transport as it is the base that is the bulky part of these scopes. When I was using one I could fit the entire lot on my backseat, so don't be afraid to save some money with a solid tube.
You should see some nice views of Saturn with it, but it will not be a huge difference compared to the 5". Atmospheric seeing is the main factor in planetary observing rather than scope size. Having said that you will be able to get heaps more DSO's with the 8". All the Messiers will become available easily and many more objects.
Good luck with the purchase.
Malcolm
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