My wife gets a few decent VISA gift cards each year. She just gives them to me and I use them for groceries until they run out. No need to think about it much. I'm sure the free money on the gift cards outweighs your credit card rewards :)
Not really. When you use credit card points to transfer to airlines for first or business class tickets, you get far more value than the standard couple of percent cash back. Using a $500 gift card for groceries would waste anywhere from 750 to 2500 points (depending on the card and rotating reward categories). That is not insignificant when a business class ticket to Europe costs around 100,000 points. Which is one reason why I can't stand gift cards that don't allow you to get cash, which is true of most of them. The other reason is that I just cannot fathom the stupidity of paying a $5.95 fee to give someone money. Why not just give them, you know,
money, for free? Checks, dollar bills, hundreds, fifties, pennies, wire transfer, zelle, venmo, paypal - I don't care, just ANYTHING other than a gift card.