I've been discussing this with the maintainer of the FreeBSD wine port.
Right now, detection of libcups.so is done by the configure script at compile time. This means that pre-built packages must either pull in cups as a port dependency in order to always enable printer support, or they must do without printer support. Pulling in cups as a dependency is expensive for those that don't want it, and so cups is disabled for everyone using the FreeBSD binary packages. You need to compile the port if you want cups support.
Wouldn't a better detection method be to check at runtime for the presence of a libcups.so (by means of a dlopen()) and enable printers if it's found, or disable them if it's not found?
The significance of this would be that a cups dependency is required to build the binary package, but the dependency is optional at runtime. And this means that printers would always work, even from a binary package install.
-jr