Brad, in the English language there are often a number of words to convey the same message. Each one has it's own nuances and subtleties. This is where conotation comes into play. Finding the right word, with the right set of nuances, subtleties and conotation is the tricky part. I've found with time, you learn them. It does, however, require that you keep your vocabulary small. Not so small as to seem a simpleton, but small enough so that you always remain in command of it. The right words, placed in the right spot at the right time will almost always convey the message you desire without sparking conflict.
There are a number of very good books written concering the English language and its use. One of the best I've read, (and it is less than 200 pages with large type

), is called "A Bawdy Language (How a Second-Rate Language Slept Its Way to the Top)" and it's by the the author Howard Richler. It's very entertaining and very informative regarding our given language, and it's a very quick read. (I did it in one 5 hour sitting).
Whatever else Brad, never worry too much about your word usage. The English language is so full of pitfalls it's a wonder any of us can get it right even 10 percent of the time.
Like the author of the above mentioned book says:
"As languages go, English is as impure as they come: rife with borrowings from other languages, contaminated by dialects and slang, tainted by curses, and confused with double meanings, euphemisms and jargon."
In other words, don't worry if you don't get it right all of the time. The language just won't allow it.