Earlier quoted context omitted.
> I trust the competence of the 37s dev team. I don't, in large part because this shouldn't be a complicated problem to solve.
Yes, in your armchair analysis that takes into account none of the issues that they've dealt with in getting where they are today, any past architectural decisions that make this particular feature difficult to implement indicate incompetence. Your confidence probably serves you well (let me guess, early 20s?), but in this case you literally don't know what you're talking about.
No.
> but in this case you literally don't know what you're talking about.
I don't need to know what exact decisions they made to be able to tell that they were poor decisions. Easy things should be easy, and when they're hard, they're hard because of incompetence somewhere in the process.
FWIW, I've worked on a site extremely similar to basecamp (but with far more traffic, at least according to Alexa). I'm not speaking from inexperience: if this problem is hard for 37signals, it's because of failures of the implementation, not because the problem is intrinsically hard. Engineers who don't recognize that are not ones whose competence I would put trust in.