Hi ToyFruit,

Welcome to SilverStripe!

> 1) I installed SS with the Windows Installer. After installing I keep getting a popup saying I don't have LIBEAY32.dll?

I think the fix is here: http://www.silverstripe.com/core-team-discussion/flat/2486?start=8#post3333

> 2) How do I set up multiple sites to use SS (each with their own admin)? Obviously the installer has set up one site in a directory on my hard drive, but how do I now set-up another site with SS - do I just copy a bunch of files, or do I run another installer??

Hmm.. I've not used the Winodws installer much. I usually just download the php installer and copy into a new folder in my htdocs folder and then run the php install script.
You may find these topics useful:
http://www.silverstripe.com/general-discussion/flat/3117?showPost=3133
http://www.silverstripe.com/general-discussion/flat/127?showPost=132

> 3) what files/folders do I need to upload to the live webserver in order for the site and cms admin to run? The live webserver already has PHP5 and MySql installed.

I think all the ones in c:\httpd\htdocs\ (mysite, jsparty, sapphire especially).

> Sorry if these are newbie questions - any help on any of these would be much appreciated. SS looks ideal and I'm looking forward to using it

SilverStripe is indeed nice. I hope things work on for you,

Elijah Lofgren