I think liability rules are changing the outside flying thing. Technically, the company that trains you (even if it's on completely different equipment) could get roped into any lawsuits that might stem from incidents or accidents that occur during outside flying. Even in the corporate world, more and more companies are saying their pilots can't freelance on the side just to remove that risk. They may still turn a blind-eye to it, but they'll hang you out to dry if something happens and say you were operating in violation of their GOM/SOPs.