Welcome 404ender. This forum is great and Alex does a great job with it.
I'm glad you decided on an hp, I personally have the ex490 and I love it. I have been doing everything you are looking to do and more!
Ok, now to answer your questions.
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1. It's easiest for me to access the server and organize my files by using the Connect to Server in Finder and entering my User Account name and password. Where do I need to put files so that anyone already logged into my home network can access them (or watch/listen if it's a movie/a song) on a computer WITHOUT needing a User Account on the MSS, and how do I direct them to do so (do I need to enable Guest access, will the folders show up in the "shared network folders" area of their OS, etc)?
You will notice there are default shares on the server called Music, Photos, Public, Video etc...
You can organize these folders however you wish. I pointed Itunes to my Music folder on the mss and let it do all the organizing creating this folder structure(Artist name\album name). Photos are kid of just thrown in subfolders based on events\dates. You get the Idea.
The twonky media server is always keeping tabs on all these folders and updating its index. For example if I browse my mss from my ps3, it will find the media server automatically and show me everything it's indexed. Newly copied items won't show up immediately. It uses DLNA to communicate with other devices on your network without having to worry about permissions and guest accounts etc.
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2. When should I actually set up a User Account for a roommate or friend rather than the approach outlined above? I never plan on letting anyone but me upload files to the MSS, so they would be read-only accounts, so what're the differences between the two approaches as far as what they allow and support?
That would be up to you. If you want your friends to be able to access the server remotely from the web interface to stream music or vids etc they will need an account (with the exception of photos that are made public via albums) and Unless you give them yours which is not recommended.
note: Creating them an account will provide them a personal folder and you can control read/write/modify access.
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3. I like the idea of having my iTunes library on the MSS so I can stream the music to any device connected to the network. However, I definitely want a local copy of the music on my laptop for when I take it with me and might not have access to the Internet. Is there any way to sync the MSS with my laptop so any new songs I add to my local library get reflected on the MSS as well, without me having to manually add new songs to both?
There's no easy way to do this. Especially when your music library gets as big as mine. The only solution I can think of is to use Synctoy or similar Mac app. It's a microsoft app that will allow you to pick the two directories and will one, or two way (sync). Google it. Then you can find its mac counterpart.
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4. Remote streaming and remote access: how does this work? Reading about it in the guide makes it seem like you have to pay and sign up for a service in order to use any of it. I'd just like to be able to host files for friends to download who aren't on my network, and I'd like to be able to download or stream my own media files that I've stored on the MSS on computers if I'm not at home. I guess hosting a website would also be lumped into this category.
You can do this. The reason the guide makes it sound like a paid service is because most people have dsl or cable internet at home. They are not given static IP's. So if you register a domain with your IP today, It might change a day, week, or months from now. Hp resolved this issue with domain registration. All ms owners get free registration thru TZO for a year and I think a discounted rate after that. (someone correct me if I'm wrong). I use the microsoft homeserver domain registration which is free and I don't think they charge anything at all (again someone can correct me if I'm wrong.) It also updates my ip automatically.
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5. How fully featured is the WHS Console functionality in OS X achieved via
http://blogs.technet.com/b/homeserver/a ... a-mac.aspx ? It's annoying to have to either reboot my computer into Windows or to start a virtual machine using Parallels just to edit the configuration and settings. Also, I'm planning on wiping this laptop with a clean install of Snow Leopard pretty soon. Should I stick with Windows XP for my Boot Camp and Parallels or upgrade to Windows 7?
Get yourself an RDP client for mac and just log in directly into the mss. That's what I do and I haven't had a problem. Everything can be done that way. As long as you know what you're doing you will be fine. Unless you need parallels for other reasons, save the hd space.
I installed PHP and Mysql this way by logging directly into the mss via rdp and I'm hosting my own Wordpress blog as well. Check it out.
http://avillacampa.homeserver.com/blog/