It seems to me that the theme here is fear. That would be a good place to start working on yourself around your fear. Everything you asked is valid to be concerned about but you can grow in all those areas to trust yourself and love yourself more.
Be smart about your choices, throw caution to the wind and live and let live. The rest unfolds with time and exprience until nothing is the same again.
I bet if you come back here five years from now you will have your own answers to all of what you asked for yourself and based on your own experience. Just go and experience. Its the quickest and most efficient way to get the answers you seek.
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