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Recommendations - Web Server

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Guys,

I'd like to set up personal website on my home server (WSE2012), and I have a few questions as I move in that direction.

1) I know I need to register my own domain, and in one of my other threads, someone told me that I'm required to have an SSL certificate. I noticed, at one of the domain registration sites, that there are several SSL certificate providers - is one of them "better" than the others? Should I stay away from any of the options?

2) What's a good, stable, bug-free, feature-rich web platform? I know that, when I configured remote web access on the server, that Windows installed and configured IIS for me. Is that a good platform? I've heard good things about Wordpress, but don't really know other platforms out there (and, for all I know, IIS and Wordpress do 2 completely different things...). I'm looking for something that will make it relatively simple to create a nice initial website (including a couple of media-rich blogs), but allow me flexibility to add additional features later on (calendar, web portal to email both come to mind).

3) Any recommendations on resources to learn web development? I have very little experience with web design (I'm wishing I would have taken a course in college), and want to learn what I need, as I need it.

4) I know I'll need to integrate the built-in web portal for Anywhere Access into whatever website I build (like Drashna did with his site). How do I do this?

Thanks for helping a web development newbie out here.

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