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Leave paper and start paywall site?

Not to rain on your parade but I would be wary of thinking you can get 500 much less 1,000 subscribers to pay a working wage (say, $10 a month?) unless you are in a large area, have a large following, and the fans are very, very loyal.

Plus, getting those types of subscribers takes weeks / months of promotion and marketing to them.

Also, running a Wordpress site is a lot more difficult than it looks, so, as noted above, consider Patreon as your funding stream.

Despite my obvious pessimism, I wish you the best of luck and applaud you for getting the f out of newspapers.

Absolutely do not use Patreon unless you want to give someone 5-12% of your income plus 2.9% of each transaction for a publishing platform that will be limited and you'll have no control over. Use Wordpress with the Memberpress plugin.
 
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A couple of more thoughts ...

I do some freelance work for a HS site. Biggest problem is getting some coaches - the bottom 15 percent - to report scores on game nights and then provide complete individual stats after video has been reviewed and "booked." My editor always sounds surprised about these stragglers. "But he's always 'LIKE'-ing our stuff!" Huge difference between hitting a button and doing something that requires a bit of effort. I think a parallel with your potential audience might hold: Anyone can easily, at no cost, "LIKE" your online coverage ... but how many of those will be willing to take the step to pay for it?

There's probably a reason a lot of BIG media companies are going the podcast route to enlarge or retain their audience. There might be a lesson there.
 

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