All fonts for commercial use have an EULA (if they don’t, don’t bother using them.)
Sometimes it’s packaged with the font when you download it, sometimes it’s on a separate page of the website, often called “legal” or “licensing.” If it’s harder than that, go elsewhere.
Always check fonts that say “free for personal use.” If you can’t get a commercial license immediately, go elsewhere. “Contact the creator” can be a long drawn out process and I’ve long stopped giving them any of my billable time. If a client brings me something where I have to hunt down the creator, that’s what you call a Service Charge.
Purchasing typefaces should be incorporated into the job cost. You don’t have to know what ones you are going to use, just that you should know to carry to cover.
Read all licenses regarding language relating to using the outline to create objects. This is aimed at “stopping” the 3D print market but it is also putting a small but annoying crimp in the sign industry. Using such a font for a logo creates all kinds of hassle. If I had my way, these fonts would be avoided as well. The wording of the licensing needs to change at the very least.
If you do work where live file handoff is required, the client has to buy their own license.
Bear in mind that “Free for Commercial Use” often means “I will break when the printer tries to process the file I’m in.” We are still getting about 20% rip failure on free fonts due to poorly constructed outline files.
Probably 95 percent-plus of the time, I’ll use the same handful of typefaces, so my type needs might not be as varied as yours.
As someone who has used Adobe products from the beginning, I still have all the fonts that came with that software. Today, Adobe’s subscription model makes most of those fonts (and more) temporarily and conditionally available to all subscribers. (I generally avoid these subscription fonts for several reasons, but that’s another subject).
Google Fonts is also a source of reasonably good, legitimate, legal free fonts. Most operating systems come with a decent selection of good fonts already installed. Some clients have in-house fonts they’ve purchased and can be obtained from them for use on their projects and then returned (or deleted) when finished (it’s important to stay legal).
If I just need a few characters for a headline, I’ll often draw or design the type myself.
Other times, font purchases (usually from FontSpring.com, MyFonts.com, Fonts.com and YouWorkForThem.com) are billed to the clients and turned over to the them upon completion of the projects. Lots of the commercial font distributors have great deals (sales) on many of their fonts. If you sign up, you’ll received notices about these deals. Several times each year, I’ll see something on one of those sites I really like, and will buy it myself for future use (a business expense and tax deduction).
What I never do is download type from the free font sites. Nearly all of these sites are disreputable. They contain many junk fonts with sloppy outlines, paths that loop back on themselves, open paths, bad hinting, extremes with no anchors, few or sloppy kerning pairs and inept hinting. Many of the fonts on these trash sites have just been scanned from type specimen books and auto-converted (pure RIP-crashing junk and illegal besides). Even more of the fonts are just plain stolen, pirated, and illegally uploaded and distributed. There are legitimate free fonts on these sites, but there’s often no clear-cut way to tell the difference. In other words, stay away from them.
You took the words out of my mouth. Also, many of the cheap free fonts won’t let you embed them in a PDF, so you may not find out until you get to the end of the job that you cannot use them. So, always check the EULAs.