I have a client who wants to start a new free monthly tabloid newspaper in his locality. In order to see if this is a viable proposition he is starting with two monthly runs of something in the order of 5,000 to 10,000 each. We'll probably be choosing two fonts; a serif and a sans serif. Question is: would you advise him to buy them? And once purchased, presumably that is the same as licensing?
Depends on the font in question. If its widely used like Helvetica Frutiger or Trade then naa don't bother. Anything else - then get him to buy it - keep a copy for your self. And if its nice - send me a copy too.
You still have to be careful about some of the licences for fonts on sites like dafont – whilst being free to download some have restrictions on commercial use. At that point it depends what the font will be used for, how widely it will be used and how diligent you wish to be. Many people will just use the font regardless but if the client is willing to pay what is often quite a modest fee it may be worthwhile doing it by the book