My take on this. Paying or doing awards redemption. I have done this 100's of times. I will list my name on the reservation. Add my best friends name to the reservation. I will call up the hotel and ask that my friend is allowed to check in before my arrival (some times I never show up) and to charge the credit card on file. I will also tell them I want either the welcome points/or amenity over the phone too. My buddy also is signed into my Marriott app via his phone for hotels that have a mobile key. Never even has to stop at the front desk.

I have never had a hotel ever tell me no. I am also ambassador so I'm not sure if that makes a difference.

Now I will note this is only in the USA. People have posted that outside the USA it is a lot more strict.

Like people have said above you have to make the choice what you want to do. Your going to have people on here that will follow the terms/conditions and you will have people on here that test the waters. Only you can decided that for yourself..