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While I certainly appreciate their upgrade pricing policy(*), with the lower-priced applications such as OmniOutliner and OmniFocus, I personally might not get too upset if I had to buy it all over for the next major version. Both apps have delivered extensive "free" development. If the next generation is really a huge step forward in functionality, the total cost isn't really that high given how much use they get. Apple sells me a new copy of iLife at the same price as if I hadn't ever owned it, and maybe they'll release a bugfix or two. If you buy Aperture or other high-end Apple software at the educational store, you get a break on the price, but have to completely buy from scratch for each new major version, no upgrade pricing. True, if you don't use the application very much, or you buy relatively late in the life cycle of a major release, it's harder to get that cost per hour of use down to where doubling it is still inconsequential.

(*) and the 30-day refund policy, and the Macworld discounts, and the new product discounts, and the "we think our customers have valuable opinions, and we want to hear them" policy, and the ...