Austin, thank you for the quick reply, both on this site to Chris and to me via e-mail!
Considering that most users of PingPlotter will be IT users, I would humbly suggest that the old label of "Install as Windows Service" used during installation is more familiar and intuitive than "Collect data in the background," although I understand that might be more intuitive for non-IT users.
While Chris installed the beta for us, I also would have opted not to enable the "Collect data..." option, incorrectly assuming that it was giving permission for PingPlotter to collect anonymous data from the use of its software to better improve it, etc.
It's also useful to note that, before we installed the beta as a service, we had a licensing issue where only Chris's user account could access a licensed version of the beta, while anyone else logged into the server (including me) would get a warning that it was using a trial license.
After he reinstalled the beta as a service, it showed appropriate licensing information no matter who logged into the server, which is what we expected from the start.