See that little highlighted button at the top of your game list that's a circled triangle pointing to the right (like a "play" button)? Click it so it's not highlighted. That'll show you your entire library.

As for "Wake on LAN", I'm not familiar with the specifics of the technology, but I'm pretty sure that's a BIOS thing, not something that can be done from a piece of user-space software - if Steam can't respond to requests from your Steam client on the LAN, I don't think it would be able to wake up the computer in response to the same kind of signal.

The "installed" button you pointed out conflicts with my suggestion as it displays all games greyed out. I do want to see all the games installed on the PC without having to restart steam on my mac after a sleep/wake cycle. Currently it doesn't show the games installed on my PC unless I restart steam and I'm looking for another solution. I'd much rather it just works, so that I can see all the games in steam installed on the PC when my mac wakes from sleep. That is my core concern.

WOL is a bios thing on the receiving computer, but sending a WOL signal can be done with any app that has that feature included. I could do it through a command prompt or a terminal window.