Problem Number 1: A couple games aren't even being recognized as games but rather some kind of media file and Windows wants to use Media Player to read them.
It depends on the game, but usually this happens with FMV games. Games like an old (Win 95) release of Dragons Lair (for example) don't run on modern computers. It was a completely back end issue (based on the video compression engine they used to run the game) and the company who made it (in the example of Dragons Lair) was going to keep releasing the game on newer hardware and had no interest in making the old versions of it work even though they technically could. At least they were honest about that, though.
In your case, I would need more info to figure out why that is. It is possible the game won't work on a newer computer, but often you just need to know how to get around the problem it's having. Often the problem lies with how it understands the code and translates it.
Problem Number 2: One game is recognized as a game with the .exe file and when I boot it up and click install, I get this:
Hmm... I have that game. It sucks so I don't really get nostalgia to play it, but I often play old games (older than that game) and haven't had that problem. The error you're getting suggests it may not be able to run on a x64 system which is a problem you usually can only get around with hacks.
I tried it myself and get the same error. It actually reminds me of an error you get trying to run the original Grim Fandango (this game has the same Lucasarts installer they used for years so it probably has something to do with that). It doesn't like 64 bit systems (it's a 32 bit installer). The only way they could get around it with Grim Fandango was basically hacking the exe. It's much more complicated than most games of that era (or older even) to get running on a 64 bit computer. I would blame Lucasarts for that.
Curse of Monkey Island uses that installer too. Thus I haven't been able to play it for years.
Anyway, a cursory glance at google tells me this is an issue a lot of people have. If I had to guess it's probably an issue with all Lucasarts games and this installer specifically. The game itself works if you can get it installed. No mention of how to install it, that I could quickly find, though *shrug*
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