Okay, here's my (long--sorry about that) story...
Growing Up
My mom has always been an active ΦM alumna, serving as alumnae chapter president, adviser for two collegiate chapters (one of which she helped get its start), and national officer. She would often take me down to one of the chapter houses where she was Adviser and introduce me to the girls who were there. When ΦM's national convention was here in Baltimore, I might have been about 10, but my mom had me putting together about 1,000 goodie bags to help out the local alumnae chapter that was "hosting" convention. Obviously, I had an affinity for the Greek system early on. Heck, I even remember one time I was making a keychain that was pink and silver, with the intent of giving it to my mom for ΦM's silver anniversary (little did I know how old the organization was). I've been on a never-ending Quatrefoil Hunt since I was, oh, about 6. (Side note: one of my mom's "favorite" ΦMs at one of her advised chapters has since gone on to become a pediatrician in the same practice as mine. When I went in for my final appointment with MY pediatrician, I got to meet her again, this time as my sister. Very cool!)
Junior Year of High School
I went with my parents to my mom's Alumni Weekend at her college. She, of course, took me to meet her ΦM sisters. At least one of the girls who was there was a collegian, so already I was being introduced to people whom I would see when I ultimately went to the same college. I even got to take the group picture... practice for all those pictures I'd be taking in college myself.
Senior Year of High School
I auditioned at the conservatory at the college my mom attended in the '60s. I stayed on campus with two girls--one a ZTA (who was actually my hostess), the other a ΦM (her roommate). I was already experiencing the whole "Greek Unity" thing.
Freshman Year of College
I attended the same school as my mom. She had told me on numerous occasions that when I joined a sorority, she would buy me a "pretty badge," so obviously, she wanted me to go through rush. It never dawned on me that it might hurt her if I joined something other than ΦM, even after she had mentioned that she and my dad would be paying my membership dues no matter which group I joined. I'm pretty sure my mom had written my rec letter the day I was born.
My RA was a ΦM, which, of course, my mom found out the second I moved in the dorm. I didn't really have any intent of going through rush, but I did it sort-of to humor my mom. On Bid Day, after the festivities were over, I called my mom and told her I'd joined another group, just to hear her reaction. It was something along the lines of "...(short silence)...Good, congrats, I hope you'll be happy, just let us know what we can do for you." Very supportive, if hurt. But then I told her the truth, that I'd just returned from ΦM's Bid Day. I think the first thing out of her mouth was "you little brat," followed by "when should I come out for Initiation?" Since then, the bond I share with my mom has grown even stronger, but I'm still glad to know she would have supported my decision to go elsewhere.
...Continued...
It wasn't until after I was initiated for at least a few months that I learned my nickname. Because my mom was from that same chapter and highly involved locally and nationally, I'd been nicknamed "The MegaLeg" during rush. Even a year or so later, I still heard that nickname once in a while. It didn't bother me, but it did make me wonder if I'd gotten a bid because of
ME or because of
MY MOM.
[snip]
The whole 'money' thing is a pain in the butt. Even my Little relinquished her membership because she couldn't afford her dues anymore, and that still haunts and hurts me to this day. Not quite along the same line as the OP, but anyway... I have a VERY close friend at church who's 17 and going into her senior year of high school. Her family is not very well-off financially. Neither am I, but because of my love of Greek Life, and because I know Caitlyn (my friend and "little sister I never had") would probably enjoy Greek Life as much as I did, I've already started a savings account just in case she decides to go through recruitment. Her mom (her main care-taker; Dad's a schmuck) doesn't much care for Greek Life, and she doesn't want Caitlyn to get into anything that might cause trouble for her... but I know better.

So when Caitlyn is ready to go off to college, wherever that may be, you'd better believe I'll write a rec if I can, and that her dues will already be paid for! Yes, I am aware that I'm crazy.
See my story above. I think my mom did a pretty gosh darn awesome job at pushing (read: not
pressuring) me to go through recruitment. She also made it quite clear beforehand that I had her love and support no matter what I chose to do. That, I think, is the sign of a good mother, a good Panhellenic member, and, generally, a good
person.