Most organizations allow silver, gold etc. supporting memberships, where companies more interested in the organization pay more to signal their support (and, presumably to a lesser extent, to get promoted more by the organization). Having something like that definitely makes sense. I don't see the point in tying it to how many MediaWiki users the company has, though. That only seems to have disadvantages: it discourages organizations with a large userbase but small support budget from supporting at all, and prevents organizations with a small internal MediaWiki userbase (to make up a random example, Wikia/Fandom is a huge MediaWiki user but their entire staff is less than 500) from supporting at a higher level.
Support level as a function of user count
Dues vs. services
I wonder if it's a good idea to mix dues and services ("guaranteed Xhr project")? Unless X is intended to be something with a way smaller monetary value than the corresponding dues, it would tie a hard to estimate cost to a hard to change income.
IMO the message this dues structure sends is that this organisation is for commercial users of MediaWiki. If you can easily afford $100, good for you. If you are a poor student (or not student; the median annual income in Mexico is $5000, to pick a place at random), who spends their weekend improving MediaWiki, too bad for you. I don't think any group with such a due system can reasonably claim that it represents the entire third-party MediaWiki community.
Which is not inherently bad; more representation for enterprise users would certainly be great, and it's easier (and more credible) to represent a more narrowly defined constituency. (And arguably the group is already almost exclusively focused on enterprise usage.) It just doesn't match the way the group currently presents itself.
Also, it would leave a gap. Again, that's not inherently bad and not something a group can be faulted for, but in that case I'd hope someone steps up to create another user group that represents non-enterprise third-party MediaWiki users.
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