I'm just kinda curious... You know how some games which are distributed on CD don't require you to have the CD in to run the game? How sketchy would it be, legally speaking, to code a launcher for such a game and run it off a flash drive?
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AFAIK "coding a launcher" is perfectly fine. CCleaner is a program that is commonly asked for here; Google Earth and Google Chrome are other examples. If I were to code launchers and bundle the app and offer that as a download, the mods would be quick to take it down, possibly suspend my access. However, launchers exist - I know for CCleaner, at least (I use it).
The stipulation, as I understand it, is that the launcher is fine if it's just a launcher. You would then download the launcher and install it, and then follow the included instructions to install the game to the appropriate folder.
Quake 3 and Unreal Tournament '99 are two games that do not require the CD to run, the latter only with the latest patch. Deus Ex is a game based on the latter which requires the CD, but can be made to not look by deleting three characters (the path to the CD-ROM drive) from a certain data file.
Now, I'm sure the legalities of running these games portably might be kind of dicey, but if you bought the game and you have it installed, and you want to take it with you on the go, the only problem I can see is that a lot of commercial software requires that you only have one copy installed. However, aside from portable apps being technically copied, moved, or unpacked as opposed to installed (a mere technicality), if you're playing it on the go, you're not playing it at home.
So, maybe.
In any case, if you make your own launcher and don't distribute it, I'm pretty sure it falls under fair use. You may even be able to freely distribute it if it doesn't contain any copyrighted data (e.g. the logo). But again, as the acronym in the title spells out... I am not a lawyer.