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Most life regrets are crashed processes. One of mine is amateur astronomy. Donated my cheapie 4" telescope to my school when I went to college, and since then have never lived in places with good seeing :(
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Might want to look at Molisse's Urban Astronomer book. Also, a 8" dob easily fits into a car trunk, and gasoline is the best light pollution filter there is. Alternately, get a good go-to Maksutov and go for planetary observations/double stars/variable stars