I guess we got to the bottom of every issue that was raised during the thread. My original question was answered! Then new questions came up and were answered, plus other valuable tips were given I will try to summarize what I learned to help others and to make sure I didn't forget anything.

1 - Best place to transfer the Amex points to pay for Hotels?
a - Transferring points to book hotels is never a good idea because they will be redeemed for less than 1cpp, Plus many times travel/hotel portals inflated the price of a room when paying with points.
b - Book the hotels whatever is the cheapest with an Amex card to collect points.
c- It is preferable to book from the hotel's original sites, because there is more reliability when dealing with travel issues, plus we will be collecting hotel points during the booking.
d - Pay the bill statements for those booked hotels and Airbnb on the Amex site with points that can be redeemed for 1cpp (In the Canadian market)

2 - If the credit card returns more points for a particular category, see if that vendor sells gift cards for other stores you shop at, so you can have a higher return of points per dollar.

3 - Stay away from gift cards that have a fee like Visa and Mastercard gift cards. I learned today that some of them will charge an extra fee for every month you have them open.

4 - Only buy gift cards with no fees, like those associated with a vendor, like Amazon, Apple, etc.

5 - Can you get away with question 2? The answer is yes because Amex doesn't have a granular view of every expending within the store. There are three tiers of details that companies shared with financial institutions, Grocery stores, and other retailers don't usually share a level of details where every item within the purchase is disclosed.

Did I miss anything?

Thanks a lot, guys for all the time and effort in helping me out understand this confusing world of credit card rewards for travel!