1) If you don't agree, don't contribute (time or money). You're doing OSS wrong.
2) Obviously Yehuda has given a lot to Rails and other OSS communities. He recognizes a problem (regardless of its origin) that he wants to fix. Posts like this will drive people like him away. I know my life is easier because of the work Yehuda has done. If you don't like it, go back to Rails 2.X, or help fix it yourself.
3) Thinking back to the Rails 2 days, things weren't dramatically better for dependencies and getting Rails setup. This project would be applicable then.
4) Posts like this will only drive away the contributions of a smart, giving person. Lots of people make a lot of money off the work the Rails Core Team has done, don't label one of them a thief because they need financial help to focus their improvements on a specific pain point.
This project says "Hey, I have helped make Rails a pain in the ass to use unless you know Rails really well. Instead of fixing this at the core level you can pay me to make something else to fix this!"
What's next? A program to make bundler work better? I expect more from a project like rails. It is like an Xbox game with zero day paid DLC. "Here is rails. Now contribute money so I can make it work as advertised!"
Personally, I don't think this is needed, but I can see why people are interested in it.
It's not like he purposefully introduced some "painful_installation" feature, and is now asking money to make it go away.
It's not even like he unintentionally introduced some "painful_installation" feature, and is now asking money to make it go away.
What he did was what every OSS contributor does. He created some tools, added some fixes to Rails, changed some stuff, proposed some future roadmap, etc. One among MANY. People used his tools and changes and adopted them because they made their lives easier.
That doesn't mean that those changes (e.g the Bundler, a way to gather requirements) can or should also solve the general problem of easy installation of a whole and complete Rails system.
And that's what he asks money to create: an easy installer for the whole system.