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1. In the rare event the cable company found out about this, does this break any terms or conditions?
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Probably. You are almost certainly not allowed to resell. It is unlikely they will ever know, however.
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2. If he got caught for downloading music or god forbid, child porn, it would be on us, not him, wouldn't it?
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The traffic would be traced back to your IP. Your wireless router establishes your own set of addresses, but when talking to the Internet, all the devices connected to that router look the same. You can see this
by looking at the headers you send out to this page. Try it from a couple different devices on your network and note how the remote address stays the same.
You could likely establish that the destination once it hit your router was his device, and not yours, but that would be on you to prove.
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3. Could he gain access to the information we are sending over the wireless network with our own computers? I'm hooked up directly to the router with an ethernet cord, could he get any of my information? This is obviously a huge concern with my NETeller, and poker passwords. Could I somehow monitor his activity?
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Yes, he might be able to capture packets and see any plaintext you are sending on the wireless side (not the wired side). But if there is encryption on top of it (a Web site using HTTPS like NETeller) you should be fine. This also makes his communication equally vulnerable.
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I think our internet bill is $40/mo, and there are five of us who split it. So that's $8/mo for each of us. If we decided to do this what do you think we should ask from him? I think $20/mo sounds fair.
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That seems decent.