'...then they're definitely not going to be Ra2-level customers anyway. There'd be no "lost" dealer sale there, as those customers would never likely BE a dealer customer anyway...'

'...Look at it this way, if a DIY customer likes the product line enough to want to expand, how can we best exploit that? What's more realistic? Punishing the motivated and brand-friendlycustomer by making them tear it all out? Or recognizing their interests have grown and welcoming them to the next tier of devices?...'

Isn't it a contradiction, learn no to be arrogant and welcome the cheaters who wanted to buy less expensive products who you think don't ever want to be a dealer customer?
Maybe you wanted to say it doesn't mean with the time being they don't want to step up to a higher level, that would make senseBecause only because we are welcoming them on the next tier it still require to rip of their existing devices.

Make a license available for an update, its price based on the number of they devices, problem solved, no chance to buy cheap products to later upgrade them for free to a dealer level, feature reach line.