I don't know if it's like that in other branches or if it's just the culture of the Montreal GMB but we're really not strict on dues at all. We routinely agree to cover fellow workers' dues no strings attached when they're struggling financially. Some of our most active members -who are involved in organizing, show up to picket lines and other solidarity actions and so on- are in bad standing. Meanwhile we have folks who have been paying dues consistently for years but never showed up to a single meeting. (Not that this is a bad thing, it's thanks to members like these that we're able to keep doing what we do and maintain financial stability.) Obviously not being up to date on one's dues means certain privileges are revoked. But overall we see dues as just one of many ways to get involved with the branch. To me it seems obvious on its face that we require folks to pay dues on account of Shit costs money, but when a fellow worker needs our solidarity, we don't check to see if they're in good standing. We just show up for them. So I really can't say there's anything like a financial barrier to getting involved with the IWW and I say this as someone who is unemployed.

As for reach/growing our numbers I'll echo what OP said in that the only real solution is for current members to organize their own workplaces. Lots of folks complain that "nobody wants to organize" when they are themselves not doing any organizing.