[whpalmer4]

I don't think there is anything feature-wise in OmniFocus for iPad that is going to force OF 2 to come out soon after. OF 1 is a very capable program as it stands right now, and it is entirely possible that you will be happy with the current feature set and have no compelling need to upgrade to OF 2 at such time as it becomes available. My guess is that we'll be very lucky if we see OF 2 in 2010. Also, Omni's upgrade pricing typically is fairly generous. For example, OmniGraffle 5 costs $100, but an upgrade from any previous version is only $40. So, if we guess that an OmniFocus update will be about the same ratio, and you get half a year before upgrading, that's less than 20 cents per day for what I think is the best GTD app (and the best customer support!) around. How hard will it be for such an app to make you 20 cents per day more productive? :-)

Just to be clear, so that no one says I can't do math story problems, that 20 cents per day represents the extra cost of the upgrade so that you can have the app today instead of when OF 2 ships, not the cost of the base level of the application. I'm assuming OF 2 will have the same base price as OF 1.

My advice is to start now, or as soon as you can devote the time (don't buy the app until you are ready to start). Keep track of your receipts so that if you decide for whatever reason that OmniFocus doesn't meet your needs, you can get your money back under their 30-day money back guarantee.