SSL Certificate setup for Web/Address Book/iCal in 10.7 Lion?

I know nothing about certificates. I plan to use my Mini server to help manage my family's computers which are pretty spread out across the U.S. My plan is to use profile manager for device management, host a couple websites (one secure for home security cams) and share address books and calendars. This is as much a geek gadget project as it is "useful" so I understand I may be creating some work for myself
Anyway, can someone walk me through the correct setup for certificates? My research is showing me a LOT of options/parameters. Due to the expense, i don't want to create one just to find it won't serve my purposes.
Also, I think i'm going with RapidSSL...$50 is the cheapest I've come across...hopefully the offer what I need?

I have just spent 30 minutes on the phone to a pleseant chap in Athens, and now have a solution.
We tried several options and the final one worked - so simple.
Click on the apple symbol > system preferences > iCloud > disable contact sync > keep contacts
Check search, in my case it worked for the first time in several weeks :-)
then re-enable contact sync as follows:
Click on the apple symbol > system preferences > iCloud > re-tick contacts > merge contacts
Search still works
Hallelujah!

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