This summer marks 20 years for my rabbi with our congregation, so there was a celebration this past weekend. It was fun, and I could tell that he was touched. Yay!
The organizers arranged for Debbie Friedman to come in. She was his songleader when he was a teenager, and he's fond of both her and her music. She joined our cantorial soloist, choir, and band on Friday night, and gave a concert Saturday night. The concert (with associated sponsorships) was a fundraiser for the congregation, and from the turnout and size of the ad book it looks like it was effective. (Of course, I don't know about the costs.)
I don't know how this has been for other converts, but my education did not cover Jewish fundraising (beyond the JNF), and it's different from what I was used to before. When the letter about the ad book came, I thought "I have nothing to advertise" because I don't own a business (unlike a lot of my fellow congregants), so I didn't send anything in. There was an option for "greetings", but that didn't register. When I saw the book Saturday night I understood -- it's more like a memento (think college yearbook, perhaps). A lot of families bought display ads that said "mazel tov" or "thank you" and then just had their names, and some people wrote little testimonials. Oh drat; I would have written something if I'd had the clue that this was appropriate. My rabbi is fantastic, and is largely responsible for my being (1) a member of this congregation and (2) a Reform Jew, and if I'd known I would have praised him in print. Now that I know how this works, I feel kind of bad that I didn't do something as an individual. (The morning minyan bought an ad as a group, so I was part of that. And they listed my name on the committee even though I didn't really do anything.)
The other fundraising aspect, at least, I grokked. You could buy a concert ticket, or you could make a (specified) bigger donation and also attend the dessert reception, or you could make an even bigger donation and also attend the pre-concert "meet and greet", or you could make a big donation and also attend a private function (held a few weeks ago) with the rabbi's family. I usually avoid hoity-toity dinners and the like; I neither enjoy playing dress-up nor want that big a chunk of my donation to go toward paying for the food. (It also feels a little immodest to me -- I'm not criticizing anyone else, just talking about how it would make me feel to participate.) But the concert add-ons felt different to me; they were just little receptions, not a multi-course formal dinner and all the trappings. I actually paid more for the evening than the price of the gala dinner I wouldn't go to a few years ago, but it felt more appropriate to me. Now, it turned out to be fancy desserts and elegant appetizers and wine beforehand, but ok. It didn't trip my "ostentatious" sensor.
But all that aside -- my rabbi seemed to really enjoy the weekend, and he was clearly touched by things people said, and his parents and other family members were able to be there with him, and those are the important things.
In response to a comment:
It might not be exclusively Jewish, but I've been told this is normative in synagogues and other Jewish organizations. That and special appeals with designated goals and pledges and so on (like PBS, but with direct individual solicitations).
In contrast, the school fundraisers I grew up with all involved either selling things at inflated prices or sweat equity (car washes, etc). I don't know what went on behind the scenes in my parents' church, but the public-facing part involved passing the plate and making general appeals. So maybe my parents received targetted letters asking for donations, but I don't recall anyone ever paying a visit for that purpose.
I knew about $100/plate fund-raising dinners and things of that ilk, but they seemed to be more for political campaigns in my prior experience. The "ad book" concept was completely new to me.