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Does this work with custom roles I have created?

Yes! Roles created through plugins like Members will be listed on Settings > Restrict Categories

Will this prevent my regular visitors from seeing posts?

No. This plugin only affects logged in users in the admin panel.

I messed up and somehow prevented the Administrator account from seeing certain categories!

Restrict Categories is an opt-in plugin. By default, every role has access to every category, depending on the capabilities. If you check a category box in a certain role, such as Administrator, you will restrict that role to viewing only those categories.

To fix this, go to Settings > Restrict Categories, uncheck all boxes under the Administrator account and save your changes. You can also click the Reset button to reset all changes to the default configuration.

How does it work when I've selected categories for a role AND a user?

Selecting categories for a user will override the categories you've selected for that user's role.

In other words, Restrict Categories allows you complete control over groups of users while also allowing you to selectively change a setting for a single user.