Hi,
Not a direct help as such, but yes, EA is 32-bit and so are Add-Ins. But I think that's a red herring. I run EA and custom Add-Ins on Win10/x64 no problem.
Any issues with deployment are usually to do not with the application but with your development setup. If you take the trouble to set up the DLL and Setup projects correctly (assuming you use Visual Studio and WiX) you eliminate all manual steps like assembly registration. At the cost of having to run an installer every time you recompile your Add-In, true, but in my view that's worth it to avoid running into difficulties like this.
If you're doing a lot of hacking on your development machine, and by hacking I mean doing things like only installing your DLL partway, running assembly registration manually and sometimes forgetting, that sort of thing, you're likely to end up with a registry clogged up with references to old versions that no longer exist. This shouldn't cause any faults as such, the registry's fairly robust these days, but it doesn't help when you're trying to track down problems like this.
So the best I can offer is to uninstall your Add-In, make go through the registry and make sure there's nothing from old versions lurking there, clean and recompile the Add-In and reinstall it.
/Uffe