I am in the same boat. I was able to get Kayak to price out SFO - MSP - SIN and back for $900 with a bunch of connections. 21,000 MQM and Diamond. Being so close, you gotta weigh the cost of the flight + the cost of your time against the increased benefits of DM.

For me it's the GUCs and Free Sky Club that add up to make the run financially worth it, any additional upgrades, and occasional customer service help is icing.