If you use CSS, just name the font in the font stack. It can be the first font or the second or third. Each device or browser will use the fonts on your list as they are on the system. If you first place the font for Mac only, Windows will by default install the second or third font that it finds installed.
If you want to place the font yourself, remember that some devices will not support certain fonts, and you still have to list alternative fonts, no matter what. Check your analytics to see what types of devices and browsers are visiting. Choose the most popular one as the main font, and then add the fonts for the rest in descending order.
There is no guarantee that any font will load. There are too many variables, and users can always remove fonts or disable javascript and other nonsense that a web designer can drive crazy.
I use a combination of hosted and installed fonts on most of my sites, especially when the design is more critical.
Jim maivald
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