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Steam issues with game downloads

Hey guys,

Specs:
Mac (Yosemite)
CrossOver 14.0

I bought CrossOver just to be able to play PC games from steam. I had bought South Park Stick of Truth and the first 3 Five Night's at Freddies. All with no problem, downloading, installing or playing.

Today I bought assassin's Creed Rogue Deluxe Edition. I went to install it and got a missing EXE error. I followed the steps via steam's website to fix this however it didn't fix the issue.

I noticed the download size is only about 129 MB.

I powered up my crappy windows laptop with a broken screen and I tried installing there and the download size is actually correct. Only problem there is I got two disk write errors and am now attempting to reset the pc (hopefully the screen comes back on my tv when I need to do something... if not... there goes that computer....

So I've been getting the steam webhelper error for a very long time and never found a fix for it. I have never had this issue before and was wondering if anyone has and knows a fix for it.

I'm left believing it's CrossOver due to the fact that steam on my PC has the actual entire download file for the game and it's only lacking on Steam via CrossOver.

Any ideas?

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