So I'm curious. If the money orders are for legit things, say paying a personal loan that only accepts checks, electronic funds transfers, and money orders, would there be ANY worry of money laundering? Especially if say I did $500 every two weeks (pay days) or something.

I can show legitimate earning of funds, purchase of a debit gift card (One Vanilla Visa gift card issued by Bancorp), and then purchase of a money order made out to a legitimate loan company. I'm well under reporting limits and I'm not making them out to myself or cashing them myself or anything. My goal is to make a rather low (compared to you guys :P) $4,000 initial spend in 90 days on a card that will ultimately be used as a daily spend card, so there will be a record of random daily small purchases as well as a $500 gift card every couple weeks.

So I guess the plan would be to go to Walgreens and use my credit card to buy a One Vanilla Visa Giftcard issued by Bancorp for $500. Then go to the post office and request a $475 or some other number that doesn't look like I'm trying to slide under some kinda reporting limit or something made out to my loan company and then mail that off as an additional payment (since my main payment is auto drawn) and burn the leftover gift card on daily crap.

Obviously this method isn't going to get me hundreds of thousands of points on a steady basis, but this should work for my small project...

(seriously wish I had known about the Chase Sapphire Reserve BEFORE I burned like six grand in the last couple months on a personal trip and holidays... I'm back into save mode now >.<)