I've never done one and won't, and like you I think it is "a tiny bit weird". Not targeting the BBs or Brian but do a lot of artists need the money? I would have no problem with members of fan clubs and the like getting a chance for a close up experience but to go along just because you have deep pockets does not sit well for me. The artists appear more money grabbing than they may be and the customer often has a negative experience.
As with everything else a well-known, famous musicians might do, it's impossible to know how much they *need* that extra revenue from meet-and-greets. My guess is that they typically don't need to do 20 meet-and-greets to actually turn any profit of any sort. It's just extra revenue. As Wirestone mentioned, an outside firm probably often if not usually administers the program. But the artist obviously signs offHn it, and they clearly don't care that they do indeed come across as just "money grubbing" in some cases (obviously one's opinion as a fan and their outlook on economics, etc. will dictate whether they feel it's actually "money grubbing").
I think the meet-and-greet thing is similar to the ticket price phenomenon. Many artists just sort of have their managers/agents/promoters just do whatever the industry standard is. I remember McCartney one time being asked about excessive ticket prices, and he said his people just look at what top tier bands/artists charge, and they just set his price somewhere in the vicinity of that. Same with the meet-and-greets. The promoter for the tour says "Hey, we have a company that does this VIP package thing that many bands do. Wanna add that on? All you have to do is let them watch the soundcheck, and then set aside some time for photos and autographs, and you get X% of that up-charge."
To try and put a positive spin on the VIP since some are dwelling on the negatives. I can understand people having high expectations. I pretty much knew what the meet & greet would be going in. It happened to be a much greater experience then I thought it would be.
I got to shake their hands and tell them all thank you. They signed multiple items for me (even though it said one small item) Blondie had a huge smile on his face as I thanked him. I shook Brian's hand and thanked him for all he and Melinda have been doing for mental health awareness (which is a cause very near and dear to me) he said Thank you very loud with a huge smile and then said "Well I had to do it!" the handler took pictures of everything so I have this all to remember forever. I didnt go in expecting to be best friends with any of them. I just wanted to pay my respects to my favorite song writer and let him know what he means to me, whether or not it matters to him i don't know. It is something I will remember though. I don't think he was put in a situation that was out of his comfort zone ( the meet and greet probably lasted 15 to 20 minutes altogether)
The sound check was about six full songs while they worked out technical bugs and bantered while we were flies on the wall. One song they didn't play at the show which was a surprise (You Still Believe In Me.) we got to sit where ever we wanted and take as many photos or videos. I met Billy Hinsche after sound check and had him sign my sheet music. Everyone was super nice and I didn't get any vibes if discontent for their fans. The show was stellar. The only issue was how Brian's piano was angled. I was directly in front of Al in the third row and was difficult seeing Brian's face while he sat at the piano.
Otherwise I would recomend this experience as long as you understand what it is you are purchasing. I am not a wealthy person at all and saved up. To me experiences are worth more then money. To me this was well spent and I will do it again next year if I get a chance!