Do I have to reinstall the software every time Notes Administrators push out changes to the mail template?

No. When WirelessMail is installed directly to a user's mail file, the WM design elements (some forms, agents, and a view) are marked "Prohibit design refresh/replace to modify" so that they will not be affected by mail template changes. When installed to a mail template, this design element property is left unchecked, so that future WM upgrades will propagate from the template to mailbox databases.