This would have been a lot more useful for some of you if I posted this in January, but oh well.
Caesars Diamond is very nice just for the no resort fees and the $100 food comp. And if you want to keep it forever* regardless of your gambling habits, here's what you do.
From your Caesars account match it to Wyndham Diamond. When your Wyndham Diamond expires in January, use your Caesars Diamond account again to match to Wyndham Diamond. And when your Caesars Diamond expires in February, use your Wyndham Diamond account to match it back to Caesars Diamond. Rinse, repeat.
*Forever meaning until they change the system, but this has worked for years.