I finally had the day off today to strip the bike down and start looking at things. There are a couple bent/chipped teeth on the crank cogs. Nothing that looked bad enough to completely ruin the riding, though. The rear cassette was a different story, the smallest cog was missing a tooth and a lot of them looked fairly worn. The inside of the largest cog on the crank also had a large amount of marks on it from the chain rubbing/slapping it. I also went to Performance and bought a tool kit today for $65, and the crank extractor did not work, the tip of the bolt was big and round, and the inside of my crank looks like a square hole. The lockring tool also didn't match up. So, today was a bit frustrating.

I also inquired to the mechanic there what his opinion on internally geared hubs was, he had some good things to say. But at the point of investing that kind of money, I am realizing it would be easier to pay a little bit more and just buy a new complete bike. Is it possible to get a decent hybrid/commuter with IHG for around $500? That's the farthest I can stretch my budget in the coming months. But, maybe the best option with my short budget is just to repair the bike I have to a rideable state and try to keep it together until I can just drop more cash.