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I don't speak for Omni, but I can point out some likely objections to your proposal:
  • the App store doesn't allow them to do discounts. Same price for everyone. This was discussed at length when the iPhone app first shipped. And if I'm not mistaken, you can run that iPhone app on as many devices as you have synced to the iTunes account where you bought it at no extra charge.
  • your proposed discount is pretty substantial if OmniPlan (reg. price $149.99) is included!
  • if you are asking to be able to run the apps on more than one computer, you can do that already, so long as you only run it on one at a time. If you want 2 licenses for everything, again, that's a big discount you're asking for. There's nothing wrong with asking for a discount, but it has to make sense for Omni to give it to you.
  • what do you do about major upgrades? Right now, Omni gets some revenue to offset the cost of developing a major upgrade, but how would you handle that in your scheme?
  • there's no real trick to buying Omni software. I have yet to find a case where you can game the price list for more than a few cents. Upgrading from a bundled copy of OmniGraffle to the latest OG Pro costs the same whether you do it in one leap or first go to OG 5 then OG Pro 5. Same appears to be true of OmniOutliner. Upgrading to an OmniPlan family pack will cost you $5 more than buying it at the outset, but that's the only such case I've found.
  • there is a substantial benefit to buying all the software you want at once, as each additional item gets you 5% off the total order price, up to a 30% discount. If you are spending $300 or more, don't forget to add a free copy of OmniWeb, OmniDiskSweeper or OmniDazzle to the cart!
  • I don't consider this to be a trick, as Omni discloses it up front, but if you want both OmniOutliner Pro and OmniFocus, there's a healthy discount on OmniFocus for OmniOutliner Pro owners (reflecting the fact that OmniFocus has its roots in a OmniOutliner Pro document + a lot of Applescript). The discount is $20, so if you are planning to spend more than $400 you may do better by skipping that discount in favor of getting another 5% taken off the overall price, but below that it works out to be an OOP upgrade for a net cost of $10 so long as you do it before you buy OF.
  • finally, selling bundles like this makes it harder for Omni to assess where future development efforts should be directed. If you have to pay some money to use an application (remember, they all have free trials), you're probably not going to do so unless you think you need the application. Your $80 in their bank account shows that you're going to use OF, and that developing it was a good move. In an all-you-can-eat scheme, how would new applications ever directly recoup their development costs?