Audio/Video Chat → What do I need? Slingbox, HDHomeRun, other?

I was wondering if someone could help guide me here.

We have 2 TVs. Verizon Fios is our provider. Both of our TVs are in rooms where a wired network connection (and wireless) is available.

Here is what I MUST have:
1) The ability to use my iPad to watch TV while connected to my LAN; i.e. in a room with no TV, backyard, etc.

2) The ability to play content stored on a server in my home onto either TV of my choice. (I have encoded many of my DVD movies to WMV files that I have put on my Windows Home Server box.) Currently, I use my Xbox 360 to play this WMV content onto the single TV that my Xbox is attached to.

A bonus, but not required:

To watch my TV on my iPad or another computer when I am away from home.

What device should I buy to accomplish #1 and #2 above? Silicon Dust HDHomerun, Slingbox, other? Ideally, I'd like to keep this to $350 and below. Cheaper is better, as long as the device quality is good.

Suggestions?

Jeff, I have been researching this over the past few weeks. My son is playing football and I need to see college games at the park on iPhone or iPad. I bought a slingbox solo and it works well with my hd cable box. Although not streaming hd it is still a good pic. So slingbox will meet need # 1 and and the remote viewing. Cost 99 for solo 249 + or - for hdpro. The bad is app is 29.99 per device. The problem is going to be the other content. If it can be connected via component cable the sling box solo will stream it but unless it has a IR control Im not sure how you would control. I didn't find a device that did everything and since streaming live tv was most important to me sling box was the way I went.
Good luck please keep us updated as you go.

Check out Vulkano Monsoon. Google it. Works well for streaming to any device.

Thanks for the replies. I haven't decided what to buy yet, but in the next month or two, I will.