Nope, you won't have to pay twice. The purchases are tied to your BB unique ID. In case, if you are charged twice, shoot a mail to RIM, they will refund. I have done security wipe for more than 20 times now. Talking of security wipe, do note RIM has some ridiculous policies regarding passwords. In case you forget Wifi file transfer password, you have to do a security wipe. There's no option to reset the password!! The default username and password (if required ) for Wifi file transfer are: username: playbook, password: password