No Todd,
The difficulty here is obedience, not nitpicking what it looks like. Pharisees love to strain at gnats and choose how and when to obey God. Partial obedience is disobedience, as is obedience that takes any account of self into it.
Your post smacks of the question once posed to Jesus, "which commandment?", and all your advising is how best to lie.
His dilemma is simply telling someone he went to use the restroom, not the details (if you read the post).
Obedience to the Holy Spirit might not look like you think it should Todd, and honestly, how often have you rationalized away obedience in something you consider a trifle, and consequently missed the perfect will of God? If your advice to someone who obviously just needs to obey is how best to rationalize their disobedience, well, I don't know what to say.
To answer your question of "how far do you go?" the answer is simple; you go as far as the Holy Spirit wants you to, no matter what religious men and their rules do or say to rationalize it away.
There is absolutely no theology or discussion in this. The issue is obey, or not. The mere fact we are in a place where simple obedience can be reduced down to minute details of how, when, what is someones business, or anything else, brings us dangerously close to the very system that crucified Jesus.
So Nav,
You can debate, discuss, rationalize, strain at gnats (while swallowing camels by the way), pacify your conscience with all the reasons you can disobey and still 'technically' be obeying; but you will become a Pharisee.
Just ignore men and obey the Holy Spirit; confess the sin and move on with Jesus, most likely in new freedom and joy in the Holy Spirit.