I used to be a font addict. I bought probably hundreds of fonts. But, when the Internet became more commonplace, it seems font companies got more and more restrictive as to how you could use their fonts. So, I investigated and inquired with foundries specifically what I could and could not do, and narrowed down the companies I purchased from considerably.
As the years have passed, so too have some of those individuals and small companies that offered licenses that were easy and flexible, IMHO.
These days, I find myself using more and more open source fonts rather than commercial fonts.
I also "cheat." I make my own fonts and then I have no restrictions on their use. I have two comic style fonts. I also have a font of my printed handwriting which I created a number of years ago to be able to print a letter that looked handwritten but that I could easily edit.
I used to create my glyphs in Illustrator as I was more familiar with Illustrator's tools, and I was told by pro font designers that it was better and easier to do it in a font editor. Turns out, they were right. The drawing tools are arguably superior than the tools in Illustrator or Designer. I have sometimes found myself looking for features or tools in Designer and then realizing they are in my font editor, not Designer.
But, making your own fonts can get addictive. I have probably over a dozen in progress.