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Most people in this hobby take a lot of care with their equipment, so you can often get good quality equipment second hand. I would recommend inspecting the equipment before purchase and if possible using the scope at night before purchase. (both of these are things very hard if you purchase new - but then you often get warranty if you purchase new). Second hand might also leave you some $ for some extra eyepieces.
I certainly recommend the Dob - 8" it offers good viewing and is easy to move around.
You should try to attend any astronomy clubs viewing nights - they usually have a range of scopes you can use - to confirm your choice. But at your price range - a Dobsonian mount is probably best choice.
good luck.
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