I'll say something I've said a number of times before, which is that one should carefully consider the "value" of Aeroplan points. Think of it like a business. When you acquire Aeroplan points, you're effectively buying them, one way or the other, either by paying a fee like with Chexy, or by spending on an Aeroplan credit card rather than a cash back card, or by selling your transaction data to Aeroplan and the LCBO. Later, you sell them to Aeroplan in exchange for travel.

For example, you could pay your rent or whatever with debit or whatever for effectively zero cost. If you pay with Chexy so you can earn points, you're paying 1.75% for those points. If one can consistently redeem points for 2 cents worth of travel, okay, that's effectively the value you're getting out of "selling" those points. But if you're willing to pay 2 cents per point, you're not generating any profit. And given that you're investing time and energy in to reading about the points game, earning the points, searching for reward flights, etc, you should want to make some profit on the exchange of points, otherwise your "business" isn't doing very well. Depending on how many points you have, there may also be time value of money to consider, e.g. I have around 2 million Aeroplan points, so anything I earn today won't be used for years. If I had a cash back credit card instead of an Aeroplan credit card, I could invest that cash somewhere, and be a few percentage points better off by the time I actually redeem the Aeroplan points. Then there's the risk you take that Aeroplan devalues your points between when you earn them and redeem them, which can happen any time. A few years back I ran some numbers and it seemed like Aeroplan points had been devaluing (or rewards had been undergoing inflation) at around 4% per year for a while. And that risk escalates the longer your time horizon on redeeming the points as well.

So if you're "selling" points for 2 cents, how much do you want to "pay" for them? For me, with a large stash of points, plenty of other things to do with my time, and a healthy dose of skepticism as to the long-term availability of attractive redemption opportunities, it's much closer to 1 cent than 2.

That general commentary aside, I don't have many expenses I can't pay with a credit card, so this doesn't look all that interesting to me. The bonuses don't look all that big, and this would require a bunch of my time. That being said, if you can do this by spending a little over $5K (the $5K that has to be spent in the first six months plus a few bucks for the additional six recurring monthly payments), you're getting almost 2 Aeroplan points per dollar spent. Add that to what you get on your credit card, and that could be 3.25 if you're using a VIP/Amex Reserve. So you're paying 0.54 cents per point in total. But you have to make sure you jump through the hoops to get all the bonus points to make that work. Is that worth the time invested?