Hi Tones,
Thanks for raising this major question. As most non-developers, despite being an active user, I am mostly a passive bystander as far as the community is concerned. I am of course highly aware of how much I rely on developers such as yourself for my favourite tools and feel strongly about finding ways to contribute towards making sure TiddlyWiki can continue to thrive.
I've been thinking about this on and off since Soren released his incredible Grok Tiddlywiki in particular, as Soren has recently released two projects that really resonate with me and has considerably empowered me in my tinkering. I finalized a one-off donation this morning after ticking off another chapter of Grok TW, but the issue is of course that supporting only one developer/documenter, especially as a one-off, feels like an easy cop out, and ideally this would have to be balanced out by something that makes sure that the key developers are also properly taken into account and contributes to some sort of long-term stability and predictability for developers.
Now, who are the key developers? Users like me cannot possibly be expected to be discerning in that matter when deciding how and where to direct their donation. Your top of mind seems to be Jeremy, Mario and Eric, as well as yourself to some extent I imagine. Let me tell me about mine. I'd mention Jeremy, Dave Gifford and Mohammed, but simply because those are names that stuck to my mind while lurking around the forum for my own intents and purposes. I would have recognized your icon, though I'd probably have associated it to Dave. There's also a guy with a icon of a wolf that I find pretty neat and some interesting mannerisms, and another one with a flat comics face that seems to be a real regular but I couldn't remember his name without checking. I never really went on the Github page except to star the project. In reality, I have no precise idea who's contributing most and I have a feeling many potential donors wouldn't either. What I have is an uninformed, biased vision of someone who couldn't possibly intelligently support an individual developer other than based on external wow factor alone or random mental shortcuts.
There are probably many more developers out there, with very different personal situations. Some would benefit greatly from more money at a personal level, while others have high paying jobs and would view this as beer or coffee money. Some, including yourself would actually be able to commit more time to Tiddlywiki or avoid dropping out by having more funds go their way, and these are not necessarily the same as the former group, and perhaps even developers that are completely out of the picture at present. Beyond this counterfactual, there's also the question of the "bang for the buck": a dollar in Iran has more purchasing power that in the US... So many questions that personally have led me to a situation of analysis paralysis regarding Tiddlywiki and yet, here I am, also a long-term monthly donator to Linux Mint. Mint provided me with an easy "set and forget" mechanism to support the community, presenting me with a nice, trustworthy black box to address my money to. It's easy to view this support through the SaaS lens too. I currently pay $5 a month, an amount I decided based both on my modest means and on what Microsoft probably managed to squeeze out of me on average when I was a Windows user. I also pay for my Internet access (a share of €18/2=€9 per month), my phone bill (€5*2=€10 for my two lines), an Internet server and domain names, and pay around €120 per year for other software (mostly as donations these days). Supporting my PIM shouldn't be any different, and I indeed used to pay for Evernote a few years ago for a much inferior product with no authentic sense of purpose. My absolute ideal solution as a user would be to have the same kind of support mechanism for TiddlyWiki, no accountability needed, just knowing the core developers have found some sort of agreement and viable form of governance would be enough as far as I'm concerned and I'd pay $10/month in my current situation, plus $50–100 per year on an ad hoc basis.
On top of that, I'd love to have clear opportunities for one-off donations, either ex-post or for earlier releases. A nice feature would be to have make this expense-friendly because many of us can file reasonable outside expenses for such things, either as independents or employees. Your prize pool idea is interesting, but I guess we wouldn't want, say, three developers to waste their time carrying out the same kind of work in triple to claim a given prize given how few you are. From a individual standpoint, I think the most promising proposal would therefore be "a list of tools you can choose to sponsor for earlier release through donations which also act as an upvote" as I find the core extremely polished for my own needs and I'd of course love to cast a vote in favour of new and shiny things that I could get to use. Your last idea, offering a private method to commission work is also of course something to consider of course. It seems there's no "Tiddlywiki developer for hire" page on
tiddlywiki.com, which seems like a missed opportunity.
Hope this helps.
Best,
R²