I must say that my experience in getting intl awards using DM has been
easier so far than getting them from MP (where I have 5x the number of
miles, alas).
The issue of timing of call may be relevant to most customers, but I
bet that the experiences of elites may be different from those of
general members.
And finally, to pipped, you should look into building your plans around the
EWR-SIN nonstop, in which Y class is acceptable.