I tried buying some of the games in the bundle and PayPal immediately locked me out of my account.. sigh.

Well don't know what happened, but if you ask BMT micro (the vendor we all use) they're very helpful to solve problems like that :)
Also there are several payment methods including Google Checkout and Amazon.

@OP: thanks for the info. Never heard any of these games before. I am interested in Planet Stronghold.

Here is a suggestion based on something Frictional Games (Amnesia and Penumbra) does that I really like. When the game is bought from the store there are 2 options that never go away. You either download a DRM-free version from the site or you get a key for Steam which has to connect once to the internet for each installation (the client is really finicky with backups I've found).

To modify that a bit just offer the option to download a DRM-free version with the whole client or the version you use now (make it one or the other if you absolutely have to). You did mention sending him a DRM-free version but why limit it to one person? As you have saw on this forum people are very picky on DRM and adding the option would shut them up and not hurt sales.