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Giving TM2 as a free upgrade probably does make a lot of sense to the developers. Textmate is hugely popular, and I wouldn't be surprised if he gets more than enough to finance what he wants to do off of its sales. And by making it free he makes sure that no one has a reason to use TM1 anymore, keeping his userbase unified and easier to handle.

It's also worth mentioning that licences from one discount bundle (MacHeist) will require an upgrade fee, a smart distinction to make.

Buttt, this is a case where he is severely undervaluing his software, which isn't helping in a market where software is already too cheap. The developers are doing less harm to themselves then they are the Mac software community.



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