Fact: The Torah is relevant in the lives of believers in Messiah Yeshua today. (If you disagree then there are plenty of other articles on the site for you to consider. This one is not for you.)
Fact: In many cases the Torah gives us instructions on what to do but not how (or when) to do it. For example: "You shall write them [these words] upon the doorposts of your house and upon your gates" - Deut 6:9. The what is clear: write them. The how is not so clear.
Fact: Messiah and his talmidim followed (or at least did not speak against) several halachic standards of his day. For example: Messiah spoke against the scribes and Pharisees for broadening their phylacteries and lengthening their tassels in order to be seen by men. Messiah speaks against the attitude they had... not what they were doing or how they approached the commandment. This leaves us with the indication that Messiah is acting in accordance with the halachic standard of his day regarding wearing tefillin ("You shall bind them as a sign upon your hand and let them be a symbol before your eyes" - Deut 6:8).
There are only a handful of options we can consider:
1) Do not follow the commandments (traditional Christian perspective regarding Torah). 2) Follow the commandments (Messianic perspective regarding Torah).
I really don't like (a) or (b) for various reasons. (c) seems like a ton of work (reinventing the wheel... a LOT) and (d) means submitting to rabbinic authorities that reject Yeshua as the Messiah (not a very palatable solution but is it necessarily wrong?).
I'm interested in feedback and thoughts from others to see where this might lead based upon your experience.