Jonathan Hoefler is always incredibly articulate about his relationship to letters and fonts. In this case, he does an entertaining and detailed job of spelling out the challenges, concerns and considerations a type designer faces when creating fonts for the web.
“There is no room for sloppiness, for carelessness, for procrastination. Every detail is important because the end result is the sum of all the details involved in the creative process, no matter what we are doing. There are no hierarchies when it comes to quality.” -Massimo Vignelli