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It has been a long time since I had my Venture, so I have forgotten a lot about it, but if the Venture has any rubber lines in the rear brake system, it may be that those sections have weakened over time and stretch or expand when pressure is applied. If there are rubber sections, maybe it is time to replace them, preferably with braided steel covering. Just a thought. This would not necessarily have anything to do with air bubbles, but could affect the ability to lock up the rear wheel and slide it, which the Venture should do very easily, as the rear brakes are known to do that even of good dry pavement.

Don't know if it applies the same in this situation, but I know a collapsed brake line can cause some problems. When you bleed at the caliper, does it seem to have good pressure?