It took me a while before I could type Pennsylvania without messing it up too badly, and even now I tend to type it once, and just copy&paste throughout the document...  But Pennsylvania's letters aren't really the problem, though.  I did manage to get used to it.  There are many states that have long names, and Pennsylvania is at least phoenetically reasonable.

Instead, I find that people here in Pennsylvania put the letters in their place names in the wrong order, so as to make it nearly impossible to really pronounce them.  I tell you, it's a pronunciation nightmare living here.

Sure we have our fair share of "English" names, such as Intercourse and Blue Ball.  Not to mention more conventional names like Phoenixville and Collegeville.  Even Norristown and Wayne are easy.  But the more I get out, the more I realize that this state's founding fathers suffered from a tremendous lack of logical thinking.

Take, for instance, Bryn Mawr.  How do you say it?  (Brin'-Mar)  Bala Cynwyd? (Bala'-kin'-wood)  Uwchland?  (Wuk'-lan)  Schuylkill?  (Skoo'-kil) Conshohocken?  All right, so you can eventually sound out the last one, but at a glance, it looks impossible.

So, I conclude having made my point, and leaving you one last stumper.  How do you think you should pronounce "Tredyffrin?"