Thanks a lot for this Link2110! Out of the info I got from this thread this is the one I wasn't walking away full of confidence. The video that I posted clearly says that Amex can see all your transactions at a granular level because they operate as a bank, if you go to your bank statement for the credit card, you can see every transaction in detail, I think rather than the tiers that maybe apply for Visa and MasterCard because they are not the banks, for Amex could be the equivalent (In a very smaller scale of course) of cheating in your taxes, you may get away with it forever because based on volumes it may be impossible to check every taxes filed, but the reality is that randoms check do happen and since you are breaking the rules, there is a possibility that they may catch you and there may be consequences.

I already looked into buying Loblaws gift cards (Since they own No Frills) or Costco and is very difficult to find places that physically sell them here in Toronto, other than going to those two stores. I have never used Rakuten but the reviews are awful, looks like customer support is none reliable and if your card doesn't work you may be out of luck, I even try their Canadian phone number to ask some questions and just like some reviewers said is just a repetitive loop of being asked to press one for English, clearly that didn't leave me with a lot of confidence in the company. On top of all of that, I read that for the Loblaws card you have to go through a tedious GC registration before being able to use it.

Let's say that Amex noticed my activity and rather than shutting down my account and blocking me from doing business with them, they send me the warning message first. If that is their modus operand I could take the chance and do the Cobalt strategy, only if the math makes sense of course. After receiving the warning I just cancel the Cobalt and go back to using the Platinum in the way I'm planning to do so right now as our daily driver.

I was trying to first figure out how to buy gift cards for those two grocery places just for the Platinum, I had the hope that after doing it for while and having a better understanding of the process, I was going to consider getting the Cobalt card and see if it could generate enough points at 5x to be lucrative. As I mentioned earlier eating out is not something we splurge on enough to have a significant impact and neither for the 2x gas because I work from home and my wife has a very short commute. We are only talking about $800 a month at 5x in grocery, plus $120 in gas a month, streaming at 3x is inconsequential because it will be $50 a month top, we are also paying for Apple Fitness Plus but I don't think they consider that streaming.

Maybe incorporating buying Amazon, Best Buy, Apple, and Home Depot gift cards at the grocery stores like some of you guys mentioned, may make the Cobalt generate enough points to pay for both card fees and leave us some extra to pay for some hotels but is going to be very difficult because cards fees alone will be $829 ($674 (Both Platinum minus $200 travel) + $155 Cobalt), so it needs to generate at least an extra $500 on top of the card fees and that wouldn't cover a lot of nights in hotels either.