I have come across several questions/answers that I would like to vote up or contribute to. However, I am not cool enough with reputation points.
Anyone know how you can be cool without asking meaningless questions?
Thanks for your interest in participating! The reputation system can be a little bit confusing at first, but rest assured - it's not that we think you aren't cool.
Start out by taking the tour. It explains all the basic concepts of how the site works. If you check out the privileges page you can see how much reputation each new privilege requires and how close you are.
There are several ways to gain reputation without just posting questions. The foremost is to post answers. There is almost certainly a question here somewhere you know the answer to. You can browse the unanswered questions list to find some. Every upvote on an answer you write is worth +10. You can also suggest helpful edits to existing questions or answers. Every approved edit is worth +2.
It won't take you long to get the 15 points required to upvote, and with a little bit of effort you'll soon have the 50 points required to comment.