Jim,
 
With respect to your concerns about NCAA regulations and their
interpretation...
 
A couple of years ago Cornell's associate director of athletics,
Betsy East, met with the board of directors of the Cornell Hockey
Boosters Association to discuss this exact subject. She prepared a
summary of her talk, in question and answer format, which we
published in the CHBA's newsletter. If I can find an electronic
version of that information (problematical at the moment, as I
just moved into a new house and most of what I own is in cardboard
boxes at the moment) and upload it to the mailing list in some
reasonable fashion, I will. It won't be for a couple of days at
least, though.
 
A couple of questions that I can answer right off the bat....NCAA
regulations apply to what they call "athletic representatives,"
a murky term which includes the obvious--employees of a member
university's athletic department--but also includes the non-obvious--
anyone who has ever made any kind of contribution to any athletic
program, for example. In the case you brought up of the mythical
"Brad", a fellow student buying "Brad" a beer may be violating state
liquor laws (if either he/she or "Brad" is under 21), but not NCAA
regulations, as the student is not considered an "athletic
representative." If an "athletic representative" were to buy "Brad"
a beer or have "him" over to dinner, that would in all likelihood
constitute a technical violation of NCAA regulations. It's an
extremely messy subject for which there are no clear answers.
 
Hope this helps, at least a little. Betsy East's information will
help a lot more, if only I can find it.
 
Arthur