Ok so there is a BIG misconception out there about what legalism is.
Biblelogic01... ::sigh::
I can tell you have a good heart. You have provided your understanding of legalism, you have asked some follow up questions to better understand others, and you probably hope to untangle some confusion on the matter. As someone who likely shares much common ground with you on Torah observance, I tried to do the same when I first joined this forum but that desire quickly diminished. I also got really busy and haven't been able to respond to a number of outstanding posts, but that's a different issue. Let me just tell you: most people here have already drawn their lines in the sand. You're simply going to find those who support your position and those who do not, with few to no people in the middle who may still be unsure on these issues. Maybe the casual reader who does not have an account or has an account but doesn't post often. But in terms of a discussion, most people are going to pick their sides quickly and stick to their guns. As unlikely it is that people on the other side will convince you to change your ways, you are just as unlikely to have much of an impact on them, especially in regards to Torah observance. But keep fighting the good fight, regardless! Just don't let yourself get exhausted over it.
On legalism, the conventional definition is very prevalent on these boards and elsewhere. The conventional definition has already been provided by someone else in the thread: Legalism is commonly viewed as anything which is not popular in the modern church or not kept by individuals themselves. If you do it and they don't, and if you feel God wills it for His children and they don't, you're likely to be called a legalist, simple as that. If it's a matter others agree with, then you won't be called a legalist. It's a term employed very subjectively.
I feel the scriptural definition is different: In the NT writings, I see legalism as seeking legal conversion to Jewish status, or some standard of Law keeping, in order to merit salvation. This is attempted through reliance on one's own works instead of the work of the Messiah. The Torah observant folk on this board will say they don't keep the Torah to merit salvation, but instead do it as a result of the grace given to them and out of their love for God and neighbor. Those in the other camp will say that any attempt to follow the commands found in the Torah is relying on one's own works and results in death. The argument goes round and round and likely no one comes out any wiser or having changed their viewpoint.
On your Sabbath thoughts, I am in agreement as far as I can see. The prohibition against picking grains and rubbing them was a pharisaical rule. Pharisaical rules are not God's Torah and are not binding. The problem is the Pharisees did bind them upon the people, even putting aside God's Torah in order to enforce them. This is the Messiah's problem with the Pharisees in many instances in the gospels. The Messiah never comes against God's Torah, but only against the hypocrisy of the Pharisees in elevating their man-made rules and traditions above God's Law.
The same goes for healing. The Pharisees had outlawed it as a form of work but the Torah never says so. The Messiah clearly demonstrates that it is good and appropriate to heal on the Sabbath. I believe the Messiah never broke the commands of the Torah and never taught against them. Viewpoints on this matter differ on this board.