"I couldn't upload both files despite following requirements. I'm not super fond of trying the third party system either and crossing my fingers that everything is going to turn out great. Hopefully it all works out, but so far...it's been a mediocre experience.
Update: I got my cards with both pictures! I got to pick up my order after work and I had them in time for the event I needed them for. They look pretty good for the price, and the gentleman who I picked them up from was very courteous. It's a bit of a maze to get there to the office, but they gave very clear instructions and I didn't have a problem. I'm glad I asked for a follow up, because it turned out a lot better than I had initially said. "