If you don't tell them they won't know. Unless both of you access the account at the same time. As far as him playing in another country goes, if you were on vacation somewhere in the world, you would be allowed to access your account from whatever country you were in, and play poker. So unless you tell them they won't know. You would be responsible for taxes on any big cash out, but as long as you collect the taxes from your friend, no problem.
Umm, no. PokerStars especially isn't stupid. These types of things are routinely investigated and detected.
And no, you cannot be a US player and "travel" to a PokerStars friendly country and play. Likewise, you cannot travel to the US and play, even if you can play from your own country.
Also, as part of the cashout process, IP checks and play history is usually scrutinized. If you do travel and play from a foreign IP, even when PS is available both at home and where you're at, then when you cashout they are likely to hold your funds until they're satisfied that you were in fact traveling and all is legit.
If you're a U.S. player who wants to play on poker stars this is how you do it.
Also no. What you describe is also a TOS violation and PokerStars Security is very good at detecting VPNs and remote desktop play. Since they run a client on your PC, it's fairly trivial to detect an active VPN or RDP session. If you kept up with poker industry news you would have heard about the numerous account seizures that have occurred from people doing this. It happened a lot right after BF and PS cracked down seriously on it. They may not catch it immediately, but they will catch it eventually, especially if you try to cash out.
And speaking of, we DO NOT condone the promoting of TOS violations at CC, so do not continue offering advice on how to do so, please.