How to Manage Fonts Without Feeling Guilty or Getting Sued?

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If you download a free font, you can use it in any design or map you want. You aren't violating copyright. If you buy a font, you can still use it in your designs and maps. Without violating any copyright.

There's different types of licenses with pretty much everything. Some allow you to use the font unconditionally, but just because you purchased it or downloaded it doesn't mean you can use it for monetary gain.

In general, personal use is fine. But that doesn't include making money with it. Licenses would vary between fonts I'm sure.