craigsa1- whether you do it online or via telesales, it comes out of the same bucket. The easiest way to see is to do a dummy booking online for a Club award ticket (miles only) and look at what dates it shows you- this is the same pot that the upgrade awards come out of. Upgrading an existing ticket offline is subject to this same availability.
As for looking at the ex-LIS fares, £1300*2 is a lot of money... looking at I-class availability as it stands now on Dec LHR-JNB I see that nearly every day the first flight is sold out, but the second flight is wide open... I9 on each day I checked (I tried the first week).
I dont really know what to advise... its a gamble, but I think I would rely on getting I-availability for the ex-LIS and I would pester telesales in Portugal from 1st Sept onwards to get the fares loaded so I could book!