Judging from older threads dealing with this issue, it's a touch and go thing. You might get offered a conning tower upgrade, or you might not, no matter how well you perform. There was a post about how to "force" the game to choose an upgraded conning tower somewhere in Subsims, but it's been a while. I'll do some digging around and see if I can find it. It's a simple change in one of the saved game's .upc files, but details elude me right now.
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Let the Beast inside you free!
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