People keep telling me that there is this wonderful area in Stack Exchange where you can ask questions called "chat" or "The Whiteboard", but it keeps saying that I need 20 reputation. I have such trouble asking questions here, I can't even get above 1 rep. How do I get to that much rep when even a little bit is difficult?
The first thing to realize with the reputation is that this is for all of Stack Exchange. If you have 20 reputation anywhere you can get into any chat room on the network. This means you could answer a question about cooking, photography, video games, the nuances of the English language (or for people learning English), travel, home improvement. The point I'm trying to make here is that there are a lot of Stack Exchange sites where you may have sufficient familiarity with the subject matter to be able to provide a quality answer to a question (I do want to stress that quality bit - don't expect to toss a sentence in a text box and get two upvotes - make sure you are taking an appropriate amount of time to write a good answer that is fitting in with the standards of that Stack Exchange site).
You could also ask questions on other sites too. You get reputation from that too. With some sites it is much easier to conceptualize a good, objective question that can be answered in the Q&A format. You've got a leaky sink? Take pictures of it explain what you've done to try to fix it and the difficulty you are having and post that on home improvement. You're trying to take a good picture of a leaky sink and having trouble with the DSLR you've got? Sit down and write a question about how to take the photograph and the problem you are having lighting under the sink and getting the right settings and post that on photography.
There is also the possibility of doing ten edits (+2 reputation each) to posts, but I personally suggest that this isn't the best choice for someone who is unfamiliar with the site or Stack Exchange because you may not be familiar with the expectations of an edit in the site, or the format for Stack Exchange as a whole.
All it takes is 20 reputation somewhere and you will be able to get into chat. There are many sites to explore where you can get that reputation, not just here.