As I've noted in previous posts, one of the advantages of living in a small Jewish community is that you don't have any of the judgemental frummer-than-thou nutjobs that make being not-Chareidi orthodox so umcomfortable. In addition, our shul is more a community synagogue than an Orthodox one in nature (although we have the whole mechitza setup) and our day school is also community based which means our children learn how to interact with and respect non-observant children without being taught that they're this strange species of life.
However, there are limitations to living in such a small community. The reverse side of the lack of nutbars is that there are very few dedicated "professional Jews" to serve as an example to folks looking to become more attached to their Judaism. It also doesn't help that the local rav does whatever he can to downplay any sense of depth or commitment to the religion when attempting his special brand of kiruv. As a result, some folks get presented with a version of "Orthodoxy" that would not be considered Orthodox in a larger community. We are all aware of FFB's and BT's but this group is one I like to call "Frum for Fun" (FFF).
The basic dynamic of this group seems to be as follows. When it's fun to "do Judaism" they are very involved. This is the crowd that shows up for davening on Shabbos and belts out the tunes at the top of their lungs. They're involved with shul projects, do lots to help out during the holidays and kiddush luncheons and are always enthusiastic participants when it comes to special events. Their sincerity cannot be questioned and they bring an amazing energy to everything they do.
And then Monday morning minyan rolls around and... they're not there.
See, the real challenge of kiruv isn't getting people out to some Shabbaton or Pesach seder. Getting people to show up for programming is easy. Ask any Chabadnik. The real challenge of kiruv is getting these same people to see the importance of being at shul during the week when it's just the routine praying that's going on. It's about getting guys to wear a kippah outside of shul and women to change how they dress when it's not Shabbos. This happens in large communities because as people progress they see other folks still further ahead and realize there's a deeper commitment than what they're currently engaged in. As a result, they continue to progress so that they can become part of that group. In a small community there is such a need to be inclusive of anyone who shows some interest in helping out that no one wants to say the dreaded phrase: "If you want to be frum then you have to change the following:" The fear is that a person will respond by heading out the door and that kind of negative outcome is to be avoided at all costs. However, in order to avoid alienating we dilute the actual commitment. The FFF's never progress beyond the beginning stages.
This works, of course, as long as these folks stay within the small community. At some point, though, there is a danger in that a FFF might move to the larger community nearby and suddenly discover that what he/she thought was Orthodox "enough" isn't. That disillusionment might be heartbreaking.
So what's better? Making people feel welcome no matter how partial their observance for fear of harming their connection with Judaism, or showing them the line in the sand where real Orthodoxy begins and presenting them with the honest limits of what's "inside the pale" and what's not?