Need some advise on upgrade strategies:

For the past 3 years, I was able to use my miles to upgrade from EWR to Asia (NRT or HKG) round trip in November. I'm planning my trip again now and can't get a outbound upgrade...

Here's what I have on hold:
Outbound: Nov. 9: EWR to HKG (economy)
Return: Nov. 23: HKG to NRT (economy) NRT to EWR (Business First)
The price for this trip is 1034.00 + 300 upgrade fee.

Question
*Hold out and buy a ticket later when upgrades seats might become available?
*buy the ticket now and ask them to place me on a waitlist for upgrade (what are the chance for that to happen)
*Still buy the ticket and if an upgrade seat becomes available +/- 1 or 2 day, just suck it up and pay the $150 change fee?