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I've been wondering this for years, especially as my collection of typefaces only inches towards becoming halfway decent. I do actually buy my software and fonts, and find it often financially prohibitive to purchase anything new or exciting that comes out.
So, for a freelancer like myself, who is not rolling in it, what is the best way to accumulate great fonts? Do you bill clients for them, and if so, how do you brace them for a couple-hundred in expenses for a typeface?