If we use "SINGLE|ANYONECANPAY" then we can each make a transaction with 1 input and 1 output which just sends our BTC to ourselves, and gmaxwell can combine them all into a single transaction. I think.
I think so too, although "taint analysis" tools should be able to exclude those transactions really simply as not being indicative of all the inputs having the same owner. Though if the point is to demonstrate how simplistic the tools are at this stage, that might be good to try anyway just to force them to adapt.