First and foremost, a serial complainer could in fact be a function of a serial failure on behalf of the airline/hotel, etc. I actually had FOUR UA trips in a row within a month of another that
1. luggage was lost AND not returned in a timely manner
2. special meals were not loaded EITHER direction after calling to confirm twice each way
3. upgrades were screwed up, again after calling twice to confirm that everything was OK
4. CSR at airport had OKd certain luggage transfer in advance in my record, but CSR on day of departure chose to ignore the record notation.

Yes, I called UA each time because I was THOROUGH in my effort, followthrough, etc. and UA just dropped the ball.

As A Million Mile Flyer, I don't need to fish for compensation. I want these problems to be avoided, preempted, etc. I explain (always nice, calm, friendly) to the (usually beleaguered)) Customer Service staff. After the explanation,I ask them how they would have reacted in the ssame situation and what THEIR expectations would be for reasonable resolution. By empowering them and trusting their discretion, I have been universally pleased with their responses...whether or not compensation is involved.

I think they can smell when you really want to resolve a problem versus milk the system.