If you are fairly computer literate, you would not have needed to contact them at all. I am by no means tech savy and it is quite easy for me to accomplish making such reservations, provided the exceptions that I have noticed when making such reservations.

Whenever you involve another person, it can be complicated by so doing -- you apparently experienced this twice. Again, had you made the reservation online for any sort of reward reservation, you would not have experienced this in a standard reward booking as the points are automatically deducted from your account and the e-cert is automatically attached to your reservation and sent to the hotel. In those instances where you have earned a Multi Category Cert, the cert will be pulled preferentially from your account for the reward reservation, instead of points. Should you wish to use points for whatever the reason, you simply have to click the radio dial which states that you want points to be used for the reservation and the multi category cert will stay in your account. It is not complicated.

Hopefully, as a fairly computer literate fellow, you will no longer need to rely on another for making these types of reservations now that you have the above.