Looking at the Wine Application Database to see if the games you want to play are supported would be a start. Sometimes there's information on how to get a particular game to work, too. Reading and following the Wine general help can't hurt either.
Personally I would get an amiga emulator but http://www.linux-gamers.net/ it is not quite as specific as the wine site
As for the pirates game it says DirectX 9 or better which wine does not do so good.
I would not suggest it just yet but you could go the cvscedega route (cedega is a commercial branch of WINE but they release some code allowing you to upgrade WINEs gaming ability a little bit). Read through the first link though before jumping headlong into it.
any search for 'linux games' or 'linux shooters' on google will bring up the most popular games. I like/have liked Planeshift (mmorpg), Urban Terror (shooter), Nexuiz (shooter), True Combat Elite (shooter), Battle for Wesnoth (strategy), etc. Check out http://gaming.gwos.org/doku.php.
Right now, all I play are CS:S and Portal through wine, and boot into windows for CoD4.
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I don't have a wii u anymore to test it myself, but if homebrews are not visible on the wii u menu I think you can press L + R + minus to open the plugin menu, there should be an option called "homebrews on wii u menu" or something similar
Or when your player dies, you can say in code, if enemy exists, do nothing, but if enemy does not exist, then create enemy at certain spot. (This would be a pain tho for lots of emeies)