Paul and the Law

1 Timothy 1
I remember when I was in college one of my dorm mates (whom everyone was afraid to debate with because he was very good at verbal sparring) made the statement that Paul wrote to Timothy because Timothy was a legalist and Paul was trying to loosen him up a bit. The conversation started because of the verse "drink a little wine for your stomach's sake." This guy's contention was that Paul knew that wine wasn't going to solve any stomach ailments but was trying to get Timothy to loosen up when it came to drinking and other issues.
The problem with my friend's argument is that when I read Timothy, over and over again I see Paul appealing to the law, the commands and the instruction of Jesus: made an apostle by the COMMAND of Christ; Timothy is to COMMAND certain men to stop teaching false doctrine; we know that the LAW is good; I give you this INSTRUCTION... so that by following them you may fight the good fight, etc. It seems that Paul, rather than trying to loosen Timothy up, is appealing to the law to restore order in what seems to be a very chaotic situation: false teachers confidently asserting things that they don't really know anything about.
The verse that stands out to me is verse 5: the goal of this command is love. I tend towards the more legalistic side of things (I come by it honestly). I fight this when it is imposed on me from outside but, hypocritically, find myself imposing my legalism on others. The problem is that the goal of my legalism is not love but obedience, toeing the line, conformity (and not to Christ but to my idea of Christianism). It would be very helpful to me if God would overwhelm me with the awareness of the grace that he has poured abundantly over my life (v. 14) so that I in turn could be a conduit of his grace to others.
My goal is to find Jesus in every passage and today I find Jesus to have high and exacting standards. He is holy and demands holiness from me. He is also full of grace and mercy. Paul received mercy because he didn't know what he was doing (v. 13). How much greater the mercy Christ has shown me because I know exactly what I am doing!