first off, what's the difference between a typeface and a font?
now that that's settled, the traditional way for designers to access fonts for professional use is to license them (referred to as a EULA – end user license agreement). licensing means you pay a fee to use the artwork (or intellectual property) of another designer, but creative ownership of the typeface design remains with the original designer or type foundry.
licensing is usually based on a number of CPUs (central processing unit, the primary element of a single computer). designers can purchase a font for one CPU, but a discount is often offered for 3 or 5 or 50 CPUs – the more CPUs, the bigger the discount. font licenses typically have some limitations with what you can and cannot do but there are few restrictions on where or how you use them once you purchase a license.
some things you cannot do:
- make additional copies for your friends (technically, this includes sharing fonts with vendors like print shops).
- tweak the font and then sell it as your own creation.
some things you can do:
- use the fonts until you are dead on print, environmental, or imagery for the web
- modify, customize, distort, color or otherwise mess with the font in your own design work
- use it on the web, provided you purchased a webfont license along with the traditional license (see below)
the somewhat recent advent of the "web open font format" (woff) in 2009 has allowed designers to specify basically any font that comes with a web license. how fonts work on the web is the subject of another post. basically, most webfont licenses allow for a certain number of pageviews per month. more pageviews = a more expensive license.
designers looking to save maximum dollars can purchase single weights of any given font, which are typically under $50 each, but you are literally buying something like "caslon bold italic" and no other weights. purchasing a family will cost more (sometimes waaay more) but you will have much greater flexibility in terms of what you can use.
all that said about the current (traditional) state of affairs, there are new approaches developing for how designers license fonts. here are two for consideration:
typekit by adobe allows designers to subscribe or purchase fonts at different usage levels and for different size organizations. typekit is actually available to you through kcai as part of your creative cloud subscription. pretty awesome. adobe distributes a range of type foundries, but not all. i have been able to purchase webfont licenses from independent foundries and upload to typekit (i have a personal subscription) so i can use custom fonts on my own websites. this site, and my other site, the new programme, both use the klavika family from process type foundry.
fontstand is a pretty awesome new setup that allows for font rentals for print and web. this is amazing as a money-saving strategy. once you download the app to your desktop, you can try a font for free for an hour (warning: no "r" available!), you can rent it for a month at 10% of the full licensing price, and if you rent a font for a year, you own the license for good. i've used fontstand to try fonts in digital logo sketches and it's great for that purpose.
i'm sure there are other creative approaches out there, but these are two that i know of right now. chime in below in the comments if you find others.