The most difficult part about freelancing is dealing with editors and getting paid. It helps if you're really good at selling yourself, getting assignments, otherwise a good reputation will keep magazines and editors knocking on your door. It's not that difficult to make a decent living at it if you hustle a lot and are able to have a good turn around time.
Also key to holding down a freelance job is having contacts in the industry you're writing about. Having a job on a magazine or newspaper for a couple years, paying your dues, making a name for yourself -- all that will help you when you decide to go alone.
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