I am a newly minted Elite (first time with status in living memory), with benefits beginning next March.

We (H/W) are thinking of a couple of weeks in Italy, and if we go are pretty much committed to YYZ FCO on June 5, returning June 20.

With the current seat sale (?) we can book Tourist (K) for $2509 return for both of us. As I understand AE*E benefits, this is a non-upgradeable fare.

Or, we can book Leisure (L) for $3457 rt for two. This is upgradeable with a SSWU within 4 days.

So, what are the chances we can upgrade on one of the two flights; of course, our preference would be the outbound, as it is overnight, but the return leg would be fine. But, I don't feel like paying the extra $1000 or so if the chances of using a SSWU are slim to nil; I would use the money I save to self-medicate prior to the long flight in Y.

Thoughts?