Just thought I'd chime in with another update as this still ranks high for PyroCMS vs OctoberCMS.
Where I work have started slowly adopting Pyro for some of our projects, and its potential is very clear - the streams platform is very powerful and flexible which is great.
The downside is still the documentation, it's sadly extremely patchy, and makes it a very time consuming task trying to figure things out. No doubt once you know it it'll be second nature but this big learning curve would be solved by real docs.
The most frustrating thing is that theres no structure to documentation at all. Some is posted as guides, some is posted in a docs section, theres no clear place you can go to submit pull requests improving them. Really it needs a decent documentation system, not a home baked one. Something like MkDocs would be ideal and would provide a much stronger base for people to contribute to. When you look at OctoberCMS (who are arguably Pyro's closest competitor) the documentation is absolutely amazing.
The whole pro situation also fees a bit poor value so have avoided that. $25 a month is expensive when you consider what October provides, and its much more active community. For $25 a month I'd be expecting some more in-depth addons, with roadmaps of what the updates will contain and when.
My view would be for your own projects, October should be considered first, and Pyro considered only if keeping to Laravel's structure is essential (although even then, October doesn't differentiate that much).
Don't get me wrong though. I do like PyroCMS very much, I just don't feel its maturing at a fraction of the rate you'd expect. The pricing of pro and very dead and half baked feeling of the website likely turns a lot of people off which is a real shame given how good the streams system is, and how dedicated to the project Ryan has been.
My (hopefully constructive) feedback to Ryan would be:
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Open the project up, make it easier to contribute to docs for a start, and get them organised.
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Ditch the home brew feeling of the site. It doesn't feel active at all. The lack of content, the very minimalist looking forum and docs being split all over the place needs resolving. Maybe have a chat with a few of the Laravel core guys such as Adam Wathan & Steve Schoger on what they'd recommend as this really is where you're losing the community aspect.
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Get some more free plugins released, and make it easier to contribute back. In the last 12 months I don't think I've seen a single free anomaly module added to the store, just little field types and things, which for 99% of people have no purpose.
I'm very much wanting to contribute with docs, modules, etc. But right now I don't even know where to start because of the minefield of inconsistencies.