Sorry for the delay! I know- it's been over a month which is really crazy. I am happy that now I have the time to answer your question: "Is Halacha for comfort? Should we only do it if it's comfortable? If it's not comfortable, how important is it to try to make it comfortable?"
Tough stuff, Michael! I have to be honest: I am sorting through a lot of ideas on this topic and don't necessarily have a set opinion on it at the moment. What I can tell you is that the halachot that mean the most to me and that I truly find beneficial to my spiritual growth are often not at all comfortable. For example, the doing m'lacha on Shabbat or holidays often makes for a lot of uncomfortable and downright annoying situations, especially this year when the holidays were smack in the middle of the week! Refraining from saying loshon hara is not what I would call comfortable but I keep it because I know that it helps me become the kind of person I want to be.
In fact, while we're on the whole issue on comfort, I just want to comment on some of the ideas that you shared in your posts. You said that you don't let certain ideas bother you, etc. Part of me is glad for you because being constantly bothered by hard questions n Judaism is not a pleasant experience, when you are expected to keep all halacha as usual. But I speak from my own experience when I say that while it's not fun, confronting these issues can be an opportunity to make things much more meaningful than they would have been otherwise. If I start to question why on Earth I need to keep Kosher, then if I decide to keep it, the mitzvah will hold much more meaning for me and will allow me to gain what I was always meant to gain from it, instead of merely going through the actions. Of course, you may decide not to keep it, which makes the decision you make all the more valuable.
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