Join Date: May 2004
Location: SIN (LEJ once a year)
Programs: SQ, LH, BA, IHG Diamond AMB, HH Gold, SLH Indulged, Accor Gold, Hyatt Discoverist
Posts: 7,735
Is traveling a day earlier (assuming the flight operates) not possible? You can press SQ to accommodate you onto that flight same as they rebooked you to 2 days later. This would be the best and they can raise that request to revenue management even if there is no more award space that day. This is "easiest" for them out of the other options discussed.
Take a day unpaid leave or so if you run out of vacation days and don't fret about an extra night cost of hotel or so. I would try that route personally, but YMMV.
Ohh and yes, so far out, locking in non-refundable hotel bookings is quite risky though I can appreciate the appeal of getting a good deal.