Whoa, I'm a bit behind on the replies. Thanks everyone. The one thing mentioned in here that I haven't looked at was the axle. I'll inspect it.
I certainly like RobP's idea the best so far
The funny thing is, I've already begun planting the seed for a new bike for next season with the wife. As usual, she just shakes her head and says "whatever." That's a "go ahead" in my book.
Still experiencing the problems btw. I haven't really tried anything more than what is mentioned in my original post. Lately, I've been just going 2 gears each time I want to shift, which 75% of the time results in one cog change. I just go two, and when it shifts one, I click back one... all of which results in a really ridiculous habit that I am forming, lol.
One thing occurred to me as I read the post about chains. I remember when I swapped out the chain, the length didn't align exactly to a link when I put it side-by-side with the old chain. I can't remember if I went a half link shorter or longer but I wouldn't think that could be causing it. Besides, it shifted fine for a while (2 months of riding 5X a week) before the problems started to occur. I think that's what makes this the most mysterious - it was fine with the exact gear for a while and this problem just started happening seemingly out of no where.
I'll be taking a look at it again later today (will check the axle and inspect hub) and will post up if I find anything.