I highly recommend going with Hyatt, which should match you to Diamond status. In 25 stays you'll requalify for the following year. I've been diamond for many years, it's a great program.

In DC you have 3 Hyatt choices, plus many more in VA and MD.

I typically get upgrades in the DC-area properties. Then again I don't typically care about my room when traveling on business, but they offer 4 annual confirmed suite upgrades which I use when traveling with family.