more helper apps see
You can connect the printer to a computer and install software on your iPad/computer to print from your ipad to the comptuer then to the printer.
Should you have some office printer that are connected to a computer there are print enablling applicaionts you can run on the iPad to print to such printers.
For Windows, try: PrintBreau, or PrintCentral.
Thanks to AirPrint Hacktivator you can turn any printer connected to your Mac or Windows PC into an AirPrint compatible printer. from:
this google query will give you more options
ipad airprint via mac
Buy another box
"The xPrintServer-Network Edition is a 'plug-and-print' hardware print server for printing from Apple iOS devices running iOS version 4.2 or higher. The device is roughly the size of an iPhone and uses the iOS native print menu. It requires no additional applications, software downloads, or printer driver installations and automatically discovers available networked printers supporting JetDirect / AppSocket, LPD and IPP protocols."
A simple and popular way to copy files.
Using iTures to transfer files:
Look in the app store for accessing Windows File servers.
Configure WebDave on your server.
This thread has good info.
How to transfer files from your iPad to your PC with iPad to Computer Transfer