I would love to hear your take on how we can improve on the first 2 aspects. I am not too worried about Rails because I use Rails and I use Padrino but despite the increasing modularity, using Rack/Sinatra/Padrino is a qualitatively different development experience.
I think you raised one of the primary issues in your response. "Padrino is Sinatra", meaning the documentation is split between Sinatra and Padrino.
There isn't primary source for Padrino (similar to Rails Guides). Also Sinatra's documentation isn't fantastic either, I often find myself jumping between blog posts, sinatra's website, "the sinatra book" constantly.
Also Rails has a much more mature community with screen casts and blog posts being produced constantly. That is probably difficult to 'create' short of DHH style evangelism.
I agree with you that our documentation isn't as thorough as Rails guides but I would argue that the Padrino guides we do have and the blog tutorial + screencast are not a bad tool to get started. I recognize though that to get started with Padrino you do need to have some basic handle on Sinatra. I would love to improve the beginner's documentation even further and I hope that Sinatra's docs get better over time as well possibly with our help.
As Florian touches on, Padrino is fundamentally about embracing the power of modularity. Understanding Rack, Rack Middleware, Sinatra, Padrino and a suite of chosen tools does ultimately become necessary. However, like Sinatra you can also learn the basics within 15 minutes. I like to think that Sinatra/Padrino can grow with you as you need it.
If anyone reading this has any interest in helping us with documentation, please let us know. Especially if you are a beginner. We are a very open community and would love some help or even suggestions on how to make our framework more inviting.
The problem is that this would mean rewriting/covering a lot of Sinatra (although I find the sinatra book/readme pretty complete). We just haven't got the manpower for that. This is the fate of a modular framework.
On my Padrino stack, I usually have to switch between roughly 20 documentation stacks (Padrino, Sinatra, Rack, DataMapper, Warden, 2-3 template languages and a lot of other Rack Middleware), so "one more" doesn't really matter to me.
Maybe some documentation on how to work with or to learn Padrino would be wise. Well, more work for us. :)
But in terms of the first 2. How can we improve our documentation, please let me know, we have a bunch of guides http://www.padrinorb.com/guides and decent (I hope) READMEs as well as a written and recorded blog tutorial screencast. Also Padrino is just Sinatra, so all the Sinatra docs here http://www.sinatrarb.com/documentation http://sinatra-book.gittr.com/ work just as well.
How can we be more effective at evangelism?