Thanks for the replies clacko, and I also now understanding the forums better.

For outbound on Thurs, Jan 12, I am looking on DL at either LGA-MSP-LAX, departing at 6:25pm, and arriving at 11:42pm (2556 MQM) or nonstop JFK-LAX, departing at 9:00pm, and arriving at 12:25am (2475 MQM).

If I choose the LGA-MSP-LAX departure above, it is not showing me any red-eyes on the return on Mon night, Jan 16. If I choose the out-bound, nonstop JFK-LAX, it is showing me red eye returns. The best option there seems to be nonstop LAX-JFK departing.11:30pm, arriving 7:45am (2475 MQM).

A few issues - I like the LGA-MSP-LAX outbound because of the extra segment, and cost (about $40 cheaper than the non-stop). Problems with that flight are it leaves earlier than I'd like (Ideally, I'd like an 8-9pm departure on Thurs) and it's giving me trouble on the return.

The issues with the nonstop JFK-LAX are losing the one segment, and also the final price. All the return options paired with the LGA-MSP-LAX (even though there are no redeyes) keep the total cost under $350. For the JFK-LAX flight (although the outbound is only $40 more) the suitable return options raise the total price to almost $600.

Another note - must be on ground in NY by 9am on Tues, Jan 17..

Here's my ideal :
- total cost $450 or less
- depart 8pm or later on Thurs
- transfer on Thurs (to get extra segment)
- redeye back to NY Mon night, preferably non-stop, or stop at night (eg LA-PHX at 11pm, then no stop in morning)

If it will make a big difference in earning MQMs, and still stay reasonably priced, I am willing to depart early Friday and take 2 transfers outbound..

Last question, if I book an early morning flight on Fri, is voluntarily bumping to a later flight with transfers going to yield more MQMs, or just some sort of voucher or upgrade on the new flights?