If you're going to create a DLL, which I think makes perfect sense, you might want to do so in a language built on the .NET framework, such as VB.NET or C#. This provides the ability to combat the 32bit and 64bit issue by building both 32bit and 64bit versions.
It's worth noting that a 32bit DLL running on Windows 64bit with Office 32bit will function just fine. It's when the user is running Office 64bit that you need to worry.
With regards to deployment, you could spend a little extra time to create an installer (using NSIS for example) to make deployment much simpler. This installer would serve the purpose of registering the DLL on the target machine. You could also make the installer install both 32bit and 64bit versions of the DLL to guarantee the DLL will be compatible, regardless of the users configuration. I like the idea of registering both bit versions to avoid the scenario where a user has a Windows 64bit/Office 32bit environment and decides to upgrade their Office version to 64bit. If you have the 64bit version already installed, the reference to the DLL will resolve correctly.