hey there. welcome to the forum. your thread is more suited to the "blogs and operations" sub-forum. i'm sure a moderator will move the thread there for you soon enough. as for your challenge, your small bankroll leaves you at a very high risk-of-ruin. i'd advise checking out some strategy threads about "bankroll management" in the beginner's digest if you plan on making a serious long-term habit of grinding the pokers. best of luck!
edit: as long as this $5 isn't money you strictly need for your daily expenses, i don't see any harm in this little challenge. however, if you plan on taking poker seriously and making some money, you're going to need more of a bankroll to be able to deal with the swings that come with poker (particularly tournaments).