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Newb Problems with AoE: Collector's Edition

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pdcumiskey Friday 23 May 2014 at 5:18
pdcumiskeyAnonymous

Hello everyone, 

I'm really new to this whole thing, and not very tech savvy, so I'm going to be very thorough in my explanation. Please bear with me. . . 
I've recently had a strong desire to play the first two Age of Empires games and their main expansions (Rise of Rome and The Conquerers), but it seemed impossible to find any way to do that without the CD's. I bought the Age of Empires Collector's Edition from Amazon and have been trying to work with it via Playonmac/Wine all day, and have had very little luck.
So far, I've only been able to install the original AoE; the expansion Rise of Rome gives me an error message stating that it can't find the original (as if it hasn't been installed).  It says to make sure that it's in its original location.  
My other issue has been with AoE2, which goes through a good chunk of the installation process before saying that it has "encountered a disk error," and it can't proceed. At first it stopped at 26%, then 96%, but it can't seem to go any further.

If anyone could walk me through this, I would really appreciate it.  If there's a better way than what I have decided to try, I'm more than open to suggestions. 
And again, I'll need you to explain it to me in the simplest terms because I'm not very familiar with how this kind of process works.

Thanks a lot for any support you can provide