When you buy a font you do not own that font you are licensing it. It is not yours to give or god forbid sell.
When you download a font (including the Free Font of the Month Club fonts) you are agreeing to the terms of the license. The license is called a EULA, the End User License Agreement.
Just because a font may be free does not mean you can give it to anyone. Others must go to my site and download it. It is a free download during a limited timeÂ from my website only. You cannot put it on your site and offer it for free. It is not freeware or shareware. All licensing applies.
When you buy a font you are paying to license that font to use in certain ways. How that font is to be used has to do with that company's EULA. You should always read the EULA and save the EULA in case you need to go back and look something up. Each type designer or company can write their EULA however they want to. They can differ greatly.
Generally a font can be used for personal use like the flyer for the church rummage sale. Things get tricky in other situations especially when you use that font on something you sell. If you use one of my doodle fonts on a t-shirt as artwork and then it is sold in a big box store you need to pay extra to do that. You need to pay me because my artwork is selling your shirt. It is adding value to your product. Obviously there are a wide array of situations between the church flyer and the shirt sold by a major retailer. That is when you email the type designer or company you bought the font from. Everyone is happy to explain their usage.
And plz do not pirate intellectual property, mine or anyone else's. If you give my font to someone instead of having them buy it that affects the amount of money I make. I am one small type designer working from home in my pjs. Your buying my fonts allow me to keep making more good fonts. This works in other ways also. For example if you have paid for and downloaded a knitting pattern plz don't give that pattern to others unless it is a free pattern. Paying the person who designed the pattern means they will make more.
If you don't contact me for a commercial license and I stumble on my work being used by you I might send you a very stern cease and desist letter. If you don't cease and desist then my 900 lb. gorilla of an intellectual property lawyer will contact you next. You don't want to hear from him. He scares me a little, alright more than a little.
Feel free to leave questions in the comment section I know this is confusing. But it is important information we all need to know. I am happy to answer your questions.