Financial institutions and governments care about any activity which shuttles money between accounts for no productive purpose. This is the essence of money laundering. They don't have the resources to evaluate whether you are doing it for some harmless motivation.
A fair point, hence why I was asking. It does seem like too much trouble for what it's worth - but that wouldn't prevent discussion, would it
Indeed, but that's a very low standard. Airlines intentionally set the retail price of miles to consumers high. There are plenty of ways to generate miles through economically productive activity.
Here I'm not sure I would agree. What would be other ways of generating miles at 0.01466 dollars per mile? Even in MR realm this is considered fairly good if I am not mistaken - and an MR implies flying to places you may not want to go to (leaving aside the fun of MRs, obviously) - not to mention potential loss of revenue from work (i.e. vacation days).