Due to sheer laziness, my maintenance amounts to an annual trip to the LBS. After moving, my new LBS suggested that I replace my chain immediately, before it destroys the drive train. What they didn't mention was that it already had, so I needed a new cassette within a week, because the chain slipped under pressure.
The next year, they checked the cassette before recommending a chain replacement, and it was already getting worn, so I decided to stay with the current chain at least as long as it takes to pay for a new cassette in the chains I'm not purchasing every thousand miles. At about three thousand miles a year, it shouldn't take all that long.
Now, though, I'm concerned that I might be causing more problems than just cassette wear. Might I have to replace the chain ring, too? Am I setting myself up for other potentially expensive problems? Is the chain likely to break in the middle of a ride within the next year or two?