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A couple career questions

Offer freelance work and see if you can edge in the door that way. In this present situation, it may require offering a less-than-market rate, since many papers are no longer taking on any freelance work. Still, the best way to force your way in if you want it. When an opening comes up, it gives you the inside track especially if you are supplying them with quality work in a timely fashion.
That said, don't overwork yourself chasing an entry-level job. If you are able to cover one event each week for a nominal fee, that's enough to help the paper out and show them what you are capable of.
 
Be able to do a lot of things. You can't only be a beat writer or a feature writer or a columnist, you have to be able to do all three, and podcast, and be comfortable on camera, and be good on social media. The more different things you're able to do well, the more valuable you are and the more you'll be able to adapt as the industry changes.
 

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