I'm a life member of HOG, but I'm not a brainless cheerleader for it who can't see the downside(s). I'm also cynical (informed? historical knowledge?) enough to know HOG was formed to benefit the dealers and MoCo by building loyalty between customers and HD/dealers. Of course, the customers have to get "enough" from it that it's worth it to them...and that's going to vary from person to person, and might change over time for each person. And I've been in good HOG chapters and terrible ones.
So here are my observations on your post:
1. Light attendance at 11:30 am on a Friday in October: School is in; it's a workday. Not all HOG members are retired or can take the day off. How's the crowd Friday night, Sat, Sun?
2. I've been to many rallies like Street Vibrations where I haven't bought the "packet" to get into the concerts and pre-paid dinners...but nearly every rally/ride has a "registration" fee to compensate the organizer for their expenses, and for some chapters it's a fund-raising event. I haven't found any free poker runs, either--by which I mean we have to pay to play.
3. As far as being a member: Doesn't everybody who goes to a HOG rally have to be a member, or at least a member's guest? What effect did that statement "already a member" have on the people staffing the rally? They might have thought you were trying to get the T-shirt and concerts for free, even though all members have to pay for it. And while I didn't hear the tone of voice when they called you "boys," it's a figure of speech, not a major put-down.
4. 95% of the attendees are HOG members. How do they provide "special" parking for everybody?
5. Predatory financial policies is right on. Ditto top-of-the-line prices and basement quality. I don't like it either. Then again, unlike with government agencies and socialist/communist countries, we aren't forced to buy anything from them. In capitalism, businesses price their goods based on a combination of their cost and the current supply and demand. Capitalism guarantees there will be competition from other companies. Indian bikes are top-quality at reasonable prices. The only thing forcing us to pay HD's prices is...us. If enough people stop buying HD, their prices will come down.
Owl, I can see you have monkey-butt about your experience there, but the HOG rallies are put on by the local HOG chapter with some help from national HOG and the sponsoring dealer. IMO, it's unrealistic to expect the local chapter to pay for T-shirts, concerts, etc. from their money. And since there are probably 35 state HOG rallies every year (some of them huge), imagine how much it would cost national HOG to provide free shirts, etc for everyone who shows up--and how many more would show up if all that was free? I don't know how much your annual dues are now, but how much stuff would it buy? Sorry, dude, but I think your crew was disappointed because your expectations were too high.