What I do is look for a Google font equivalent: https://fonts.google.com Usually there is one that is spot on or at least “good enough” and then as far as I know you can use them unlimited, anywhere. I have like 1000+ .TTF files from the Google font repository.

Google Fonts make it quicker and easier for everyone to use web fonts, including professional designers and developers. All of the fonts are Open Source, which mean you can use them in every way you want, privately or commercially – in print, on your computer, or in your websites

All free!