My philosophy for Free/Open Source Software comes down to this: that others can take what I do and do something awesome with it.  Since I don't know what you'll need, I hand you every capability I have to get you started.  Others granted me that very power to get where I am, so I seek to increment that.

It's not always simple to do: sometimes you build it, and nobody comes.  My experience is that clear code, convenient install, documentation and useful functionality all help.  An encouraging welcome helps even more, as does getting the software out in front of people.  It's all about avoiding or lowering barriers.

We accept some barriers to modification which are reasonable: if you modify the software, I don't have to support it.  If I make you sign a support deal which says I won't support the software (even unmodified versions) if you modify or redistribute the software, that's not reasonable.  If you get fired for publishing pre-release modified copyleft source code, that's reasonable.  If you get fired for publishing post-release, that's not.

The hardware and electricity costs are barriers, but they're undiscriminating and reasonable, so we accept them. Even the GPL explicitly allows you to charge for costs to make a copy. The software cost of the system is also explicitly allowed as a barrier.  The software costs of the build environment are also accepted barriers (though historic for most of us): again even the GPL doesn't require your software to be buildable with freely available tools.

As this shows, your choice of licensing is among your arsenal in keeping barriers low for co-hackers (who are not necessarily contributors!).  I believe copyright gives too much power to the copyright holder, but as copyright is so hard to unmake, I favor the GPL.  It tries to use legal power to meet the aims in the first paragraph: to force you to hand onwards all the pieces I handed to you.  It's also well understood by people and that common understanding gels a community.

Yet, as I alluded at the top, there are a realm of barriers which licenses don't even try to address: the code could be an unmodifiable tangle, the documentation awful, the installation awkward, or the trademarks invasive. A license can't make coders welcome newcomers, be friendly to upstream, responsive to bugs, write useful code or speak english.

The spectrum of barriers goes roughly from "that's cool" through "I'm not so comfortable with that" to "that's not Free/Open Source".  It's entirely up to your definition of reasonableness;  only in the simplest cases will that be the same point at which the license is violated, even if that license is explicitly drafted to defend that freeness!

So, don't start with an analysis of license clauses.  Start with "is that OK?".  Is there a fundamental or only a cosmetic problem?   If it's not OK, ask "does it matter?".  Is it effecting many people, is it setting a bad example, is it harming the project's future, is it causing consternation among existing developers?   If it is, then it's time to look at the license to see if you can do anything.  Remember that the license is merely a piece of text.  It can't stop anything, it can only give you leverage to do so.  It certainly can't make using the law easy or convenient, or even worthwhile pursuing.

To close, I will leave the last word to Kim Weatherall, who once told me: "if you're spending your time on legal issues, you're doing it wrong".