Font licensing varies based on the specific End-User License Agreement (EULA) in place by foundry that has the rights to sell the font. Fonts are treated similarly to software in that the license usually requires that each entity (individual or organization) owns their own license. There is also usually a limit to how many machines the individual or organization install the font on (usually 1–3 for the basic license level). This can be fairly expensive, but type designers play a big part in making the results awesome and designing really good typefaces is mind-bogglingly difficult.
Just like the rest of the hardware and software we use to do our job, we have an internal budget that covers the fonts we use for our client work. Our clients do not need to purchase their own font licenses unless they wish to use the fonts themselves (we try to give clients an estimate ahead of time). For example, often the client will want access to the fonts in order to correspond on branded letterhead. Most clients decide to purchase at least some of the fonts we use for their identity, in which case we provide recommendations on the weights, versions, and license levels that are best for their needs.
A webfont license is typically sold separately from a print license and is assigned to a web domain instead of an individual or organization. As the owner of the site domain, the client must always factor webfont licensing into their website budget. This can be in the form of a recurring fee, or a one time purchase for life. We’ll work with the client ahead of time to make sure our site design strategy falls in line with their webfont budget.