Wine, works for a lot of programs but some just don't do well.
If it is only one program I would try wine.
But if it doesn't work you should virtualize. Make sure you have some memory in your ram (2 gb is preferable if you run a desktop virtualized). You can then asign 1gb to your virtual machine and have 1 gb left for your debian.
Vmware server works fine but try virtualbox (it is bit more work to get usb features installed but it also can run vmware appliances).
install then the puel version (free for personal usage, also in business environment)
it has a seamless mode so you see the windows of both desktops mixed through eachother).
Probably you should try virtualization anyhow : it has huge benefits.