I struggled with this as well last year and after much personal coaching by PremEx decided to go for UAL 1K and maintain an AS account as a catch-all for any AS, NWA, CO, AA, TWA, or KLM flights. As it turned out I was able to make top status on both UAL and AS for 2000, because the first class bonus miles I received from NWA counted as status miles on AS. If you don't fly a whole lot, however, I think top status on one airline is better than mid-level status on two.

I would definitely save my one time comp for a time when I really needed it, i.e., moving, changing jobs, etc.

I am also Hilton diamond and did request comp status to Starwood diamond. I will try them both and should requalify on both, but if not, I'll pick the one that gives me the best upgrades and service and run with it.

With regard to RCC membership, you could always pay with miles. I also have a friend whose company was adamantly opposed to paying for membership until she happened to check her e-mail while a guest in the club and was able to solve a problem so quickly that it saved her company thousands of dollars. She then gently reminded her boss of this incident until he finally gave in.