Hey folks, thanks for the advice and much appreciated. I didn't know that you could use miles for flights after expiration, nor did I know that silver can upgrade on board.
Skywardhunter, could you please clarify how you can still upgrade at check-in if seats are available, even if there's no upgrade availability? I thought the latter would be dependent on the former.
My plan was to book 2 economy tickets outbound to HKG, use my soon to expire silver status to get into the lounge to make economy more bearable, then after the miles from these flights post into our accounts, pool the miles together along with additional miles from Marriott and SPG hotel stays to fund 2 upgrades from either flex or flex plus Y to J on the inbound. I have more than enough miles in my AMEX or SPG accounts to cover the difference but I don't wan't to use them when I know I'll be receiving more skyward miles which could end up orphaned after this big clear out.
However, my plan has hit a snag when talking to the EK call centre after realising this all hinges on availability. The DXB-EU leg is very low on availability on the only date that would be upgradeable for both sectors from HKG all the way to EU. To upgrade both sectors works out cheaper then upgrading each one individually. Annoyingly the Outbound has no availability so I can't even rinse those miles out straightaway.
The EK call centre rep did confirm that you can cancel an upgrade and receive a full refund of the miles, so I could just upgrade the few remaining DXB-EU seats and if every skywards miles posts in time and HKG-DXB upgrade is still available, then cancel the final sector and upgrade the whole inbound. BUT, then I'm at the mercy of the auto upgrade/waitlist whereby someone else snags my previously held seats upon cancelation.
What would be the most prudent way of not ending up with egg on my face and more skyward miles that will expire soon?
TL;DR - I'm going to HKG, economy outbound, wan't to maximise miles earned from outbound flights and partner hotel stays to fund inbound upgrade but availability is low on final sector back to EU so risk losing out if wait too long.
I could choose another EX-eu destination that's less busier I suppose.