One of the tricky bits that we should figure out on the front end is who specifically is in the crowd and what rules come with spending their $ besides an inclination to do so. I don't know much about spending rules except that there are often many arcane ones when that money is institutional in origin.
We could of course figure out something that looks like public crowd funding like kickstarter for one bit and something separate for institutional collaborative funding. Even just selling T-shirts maybe.
I like thinking that we could keep the ball rolling, putting together funding here and there to get small features, and do enough of it that say we knew there would be enough to pay a developer part time a couple years out. This seems a bit easier and more flexible, fitting to this project, than figuring out a master plan for monetization.
If you are out there writing grants for this sort of work, I would definitely recommend writing in some for dev work and technical and server support. @djgagnon has rates for his team figured out pretty well, and a line item for monthly ARIS server uptime—budgeting friendly. I've done this previously though not landed those grants yet. You'll feel like you're helping the project and also paying to make sure there's some help there when you hit snags or that ARIS really does have the feature you need when you need it.
But maybe too there are models out there we could go after that we haven't really tried yet. Consulting at scale maybe. I think there's a lot of people out there who would really appreciate this tool in their lives, and when they find it, they are often willing to spend some money to get trained etc. I think active advertising and market research would help more opportunities come up to tell the story of ARIS and what it could to to these potential audiences and offer training. Trainers could be recruited regionally and a deal could be set up where the trainers get paid for their time and some amount goes to ARIS development too. I don't know for sure, but I could see it being a straightforward sell to say that in addition to the fee paying for someone's time and experience, it was directly supporting this free and open source project. If there was some structure to this so that the recruiters and those who pay for training feel that their money isn't just disappearing that would be more attractive.
Even just putting together a quick list of people who are qualified (what does this mean?) and potentially willing to the point where we can say on the ARIS website that you can ask for this and a ballpark for rates. Right now a person has to get to know us pretty well before they even know that they could get help and that we could use some help too.