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Hi Chris and welcome to IIS. I can't respond to your post from an imaging perspective as I am only into visual observing and I'm quite happy to look at other people's wonderful images. I'd be going for the big dob myself. I think though that your post is very interesting and the thing that I would add is that you have separated the components of your interest ie results, camaraderie, equipment and optics challenges etc. Maybe the combination matters. For me if I were to go into imaging, all would be important and I would not be very happy with results that are not good quality, but it wouldn't just be results that would drive me.
Just some thoughts from the sideline.
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