You certainly can if you want to as I see you've been told. If you did it in two different accounts, who would even know? Ameritrade, and maybe some other brokers, though doesn't let you in the same account.
And yes, when you are short, you get the priviledge of coughing up the dividend to the person you borrowed the shares from. It's bad enough that INTC keeps going the wrong way, but I had to shell out $20. :(