Self Signed SSL to secure remote Mac App use?

I wonder if anyone here uses a self signed certificate to secure their use of the Mac client when you're off your LAN. This is something I do relatively often, and doing it in the clear makes me nervous.

If you are doing so and didn't make it work just because your brain is huge and you configure Apache for fun as a hobby, I'd love any handy guide you can point me at for this. There are a ton of results for a search of "self signed SSL certificate install" but not all guides are equal.

Would an easier way to secure that connection be to run a vpn connection from your Mac book on strange WiFi back to your home router. That way everything is encrypted? And from personal experience setting up vpn is much easier than SSL certificates.

Good point!