I think the article had a good point when it mentioned that the issues that are trying to be resolved stem from projects that were led by the guy trying to raise the funds.
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.