It is a fine line we walk. Clearly, if we don't OC for fear of not being able to OC, we've already lost.
OTOH, pushing for too much, too fast can backfire. Consider how certain "immigrant" rallies a couple years ago really gavalnized oppositiong to any kind of amnesty for illegal aliens; just the OPPOSITE result the organizers and participants had hoped for.
Similarly, gay rights activitsts are counseling AGAINST any new lawsuits right now having recognized the effect the Massachusetts SC ruling on gay marriage had on elections a couple of years ago and hoping to avoid a repeat with the recent California SC ruling and this year's elections.
I do think firm, steady, incremental change is needed. I hope any lawsuits filed to build upon Heller are VERY carefully conceived to advance RKBA, rather than provide the court too easy an opportunity to roll back Heller.
Of course, what may be necessary in one setting may not be in another. Here in Utah, for example we have VERY strict State preemption that is very well supported. So forcing local government to comply with that law by repealing local ordinances that contradict it, removing anti-gun signs, and the like is a pretty safe bet. I think we start to take risks if we try to force private businesses to drop their anti-gun, but perfectly legal policies.
In any event, the cautions in this article are well worth considering.