Just a word of caution: If your customers are on Windows, using Gpg4win might not be a very smooth experience. I just helped someone to install that package and I found the UX to be really suboptimal. For one, it’s GTK-based, which makes it stick out like a sore thumb in a Windows environment.
Yep, that's part of the risk of this. I thought about that, but decided to give it a go on the basis of thinking that the people using this service will be pretty tech savvy, and will be OK with installing and using some variant of GPG or the commercial PGP. If that proves not to be the case we'll come up with a different approach.