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Does Having Windows(R) Installed Elsewhere on a System Help WINE Operate?
It may, depending on the application being run. As mentioned in the section describing winecfg, some built-in WINE DLLs and other libraries can be overridden by providing a path to an alternate version. Provided the Windows(R) partition or drive is mounted to the FreeBSD system and accessible to the user, configuring some of these overrides will use native Windows(R) libraries and may decrease the chance of unexpected behavior.
Where is the Best Place to see if Application X Works on WINE?
The first stop in determining compatibiliy should be the https://appdb.winehq.org/[WINE AppDB]. This is a compilation of reports of programs working (or not) on all supported platforms, although (as previously mentioned), solutions for one platform are often applicable to others.
Is There Anything That Will Help Games Run Better?
Perhaps. Many Windows(R) games rely on DirectX, a proprietary Microsoft graphics layer. However there are projects in the open source community attempting to implement support for this technology.
The _dxvk_ project, which is an attempt to implement DirectX using the FreeBSD-compatible Vulkan graphics sub-system, is one such. Although its primary target is WINE on Linux, https://forums.freebsd.org/threads/what-about-gaming-on-freebsd.723/page-9[some FreeBSD users report] compiling and using dxvk.
In addition, work is under way on a https://www.freshports.org/emulators/wine-proton/[wine-proton port]. This will bring the work of Valve, developer of the Steam gaming platform, to FreeBSD. Proton is a distribution of WINE designed to allow many Windows(R) games to run on other operating systems with minimal setup.
Is There Anywhere FreeBSD WINE Users Gather to Exchange Tips and Tricks?
There are plenty of places FreeBSD users discuss issues related to WINE that can be searched for solutions:
https://forums.freebsd.org/[The FreeBSD forums], particularly the _Installation and Maintenance of Ports or Packages_ or _Emulation and virtualization_ forums.
https://wiki.freebsd.org/IRC/Channels[FreeBSD IRC channels] including #freebsd (for general support), #freebsd-games, and others.
https://discord.gg/2CCuhCt[The BSD World Discord server's] channels including _bsd-desktop_, _bsd-gaming_, _bsd-wine_, and others.
Other OS Resources
There are a number of resources focused on other operating systems that may be useful for FreeBSD users:
https://wiki.winehq.org/[The WINE Wiki] has a wealth of information on using WINE, much of which is applicable across many of WINE's supported operating systems.
Similarly, the documentation available from other OS projects can also be of good value. https://wiki.archlinux.org/index.php/wine[The WINE page] on the Arch Linux Wiki is a particularly good example, although some of the "Third-party applications" (i.e., "companion applications") are obviously not available on FreeBSD.