Already spending waaaay too much time on this. Using it to top off kids Delta accounts with orphaned miles to try to reach 25k (not that useless Delta/NW miles are ever really redeemable for 25k awards when you need them). I am really not going to do screen shots and printouts and spreadsheets (that is where I draw the line) and if it doesn't work I won't shed a tear.
One interesting question is whether the gift cards bought for miles for one person would result in an additional qualifying miles purchase when redeemed (in conjunction with a purchase) by another person. Anyway I bought two $5 Sears gift cards and redeemed them for something I actually need on Lands End website. Sears is on the list but Lands End is not-- and although the sites are affiliated the same jacket was $5 cheaper on the Land's End site-- so I bought it there using the Delta portal for 6 miles per dollar and no bonus. Anyway the interesting thing is that Sears gift cards are apparently redeemable by their partner sites, so you don't have to force yourself to buy something from Sears...