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I already had a $5 DigitalOcean droplet running for experimentation and stuff but really wasn't doing much with. When my wife wanted a e-commerce store for her craft/jewelry business, I figured why pay $20+ per month for Shopify or Weebly when I can just install WordPress and WooCommerce and be good to go. So I spent an hour or two getting it set up and had the basics going.

But she hated the web-based admin interface and it was way too cumbersome to get anything customized, products added, etc. In the end it just wasn't worth it and she's now on Weebly. Shopify and Weebly have their own faults and can definitely be a pain if you want to do anything off the beaten path, but for the non-technical user who just wants to sell things I see the value over a self-hosted Wordpress install.

That's fair, the UX for Woocommerce does need a bit of technical hand-holding. Could be improved on, though it seems like the pressure from Shopify will force some improvement on that front.

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