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I basically want to feel comfortable about fighting someone random.
That never happens as a result of training in my experience. It is only through countless Street fights that you learn what you can do and what others can do to you. It's entirely not worth it.
I have been a bouncer off and on for 20 years and got in to a fair few fights growing up. As an adult you can pretty much just avoid fighting entirely, it takes two to tango generally and if you're not an arsehole you don't get picked on. If you're worried about being jumped while out clubbing just go to nice places that aren't full of fucking trash.
Answering your question I would absolutely do boxing once a week, because it's fun and worthwhile.