A few times when customer has a device with no SSL option I've helped them setup an account with inbox.com
I think it is $8.88 per year. You can use it for free if you don't mind ads in the emails.
Re: Stunnel, yes there needs to be a PC that does not get turned off, or is at least on during work hours. The application can run as a windows service ensuring that it starts with windows. It's really not hard to setup once you know how. I would download the windows installer and get it going on a workshop PC. The hard part comes in editing the configuration file to do what you need it to do.
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