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Upsells can be tricky or fairly easy and I personally do not think they indicate lack of pride.
You just need to know if the upsell will compliment what your members are after, if it will compete with you and possibly cannibalize your members area, or if it is an entirely different segment of the business in the first place. It will also help a great deal if you as the site owner not only check out the site your sending traffic to (and often randomly in the future via your link). I have also found out it helps a great deal to clearly indicate areas that take you off site or banners clearly for what they are. I would never have a off site banner showing up in my members area without it saying it was an advertisement.
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