In my opinion, font handling has been -- and still is -- one of the trickiest part of my TeX experience. With font handling I don't mean using the fonts provided by a particular TeX installation; on the contrary, I mean installing and using new typefaces into TeX -- and ConTeXt. Nowadays things are way easier: both XeTeX and LuaTeX provide simple font interfacing and intuitive OTF feature leveraging. ConTeXth can use these engines too, with LuaTeX becoming the default engine for ConTeXt.
So why stick with pdfTeX? The main reason is that changing typeset engine leads to slightly different outputs in most cases, and plain wrong output in some cases. The most blatant gotcha is, in my humble opinion, when we typeset a document in two columns and want to lay out a float spreading the whole page width. If we use pdfTeX or XeTeX as typesetting engines we can use \startcolumns..\stopcolumns and place a floating object on the top of a page; if we use LuaTeX, we must use columnsets or we just can't do it. Moreover, while XeTeX is far easier to use (I used it to typeset some long documents) allows for inferior typographic control. This leaves me with only one choice: ConTeXt + pdfTeX, with its complex font handling mechanism.
