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Don't cloak, don't lie, don't attempt to cheat.
Divulge all information and all should be fine. Create pages relative to your topic. Don't stuff keywords. Don't even bold them (and I would even go as far as to link them) in this day and age. Use your verbiage naturally.
I don't think Google has anything against making money and advertising at all. I just feel that (like yourself), people think things through way too hard, which in turn ends up making your site look shady.
As far as using something such as: site.com/out/sponsor - I see no problem with that as it could be a tracking system. There is no reason for Google to penalize that unless of course you are linking to something already on their watch list.
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