It seems like there are two paths to becoming a cruising oriented sailor- either by leveling up skills from small boat ownership, or paying for someone else to handle all the boat stuff. That's an over simplification, but I'm trying to illustrate two difficult barriers to overcome for a club.
The club I belong to is on a lake, so not cruising oriented, however we can't survive with 110 Catalina 22s. We accept boats up to about 34ft and we like the revenue associated with those larger slips.
The difficulty we face is similar, an aging group of sailors with "larger" boats. Most, if not all of those older sailors started with Thistles, Lightnings, Flying Scots, so we acknowledge small boat sailing as one path to sustainability.
Probably our best program has been a youth sail camp, which has resulted in about 15 families buying boats because the parents saw it as a fun outdoor hobby to share with their kids, but most of those people are buying 22-25 foot boats. We still would like some of those parents to get interested in buying larger boats, so we do what we can to encourage overnighting, rafting up, and we are an ASA 101/103 school because we want to encourage them to grow their skills (and we hope, grow their interest in boats that are a little larger). It's not all about revenue from larger boats, but rather we are trying to provide a way for people to sustain the club by becoming attracted to boating that is "cruising" (if that can even be called a thing on 11,000 acres of reservoir). We don't specifically need larger boats, but it makes our budgeting easier.
So I've been thinking about this since the thread started, and I would say based on my experience that it's important to recognize that cruising occupies a place on a sailing continuum, and it probably isn't the kind of thing people usually do as beginners, or at least it isn't where I sail. If a club doesn't have space for other types of boating like we do, then I'd guess the next best option is to link up, partner with other programs or clubs to cross pollinate, for lack of a better term. Secondly, I believe the club may need to find ways to encourage and support sailing that is not just cruising. That may be a deal breaker, but if getting people to participate is the goal, then feeding them from the hand may require some casual racing, or day sailing activities.