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Just wondering the best practice for serving custom CSS files? File dir location for files as well as best way to link said files?

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You should add display:inline-block; to the blocks that should display as inline, not the divs above it. The following css makes them align horizontal.

.widget.widget-static-block {
  display: inline-block;
}

I also see your stylesheet: style1.css doesn't get loaded. you should check that out. As an advice on your problem. If you might think you should brush up your css and html skills a bit, i suggest you take the free css and html course at the link below. It's fun trust me.

https://www.codecademy.com/

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