An update here. I took all the advice from this thread, and came up with the following :

Fri, Jan 13 - LGA-MSP-LAX - 6:10a-11:10a - $200 - 2556 MQM
Mon, Jan 16 - LAX-SMF-ATL-LGA - 4:32p-8:51a (Tues) - $345 - 3354 MQM

Total Cost - $545
Total MQM - 5910

Not bad considering the standard one transfer each ways which Delta provides yield a cost $555 and total MQM of 4955.

FYI - I could have increased MQM even further (up to over 6300), but wanted to stay reasonably priced.

I used http://fly.qux.us/smcalc/ to get an estimated calculation of NYC-LAX with different transfers either one way, or both ways. Once I narrowed down which cities yielded greater MQM than just NYC-LAX non-stop, I spent a few hours plugging those combinations into Delta.com. I am glad to have my results, but was there a more efficient way of doing this? To consider price in addition to MQM, I could not think of any better way.

Lastly, thanks for the info re upgrades wo Elite status, Crimson. Does that also apply to trying to upgrade while at the airport in person, or just when booking in advance?