A person in an enviable position.
There are apparently multiple, in fact, almost infinite, categories of titmoe.
The etymology and current usage of this word was discussed in SV podcast #8, starring the aforementioned Mr. Darin, and convieniently entitled, "Titmoe", after which, it was NEVER HEARD AGAIN.
 This probably has something to do with it being a word that was used among AAl's high school friends, long before Matt was even born. Further, there just haven't been all that many titmoes to use it on.