My task management dilemma

The arrival of my iPad next week has had me thinking about how many different ways I'm going to be able to use the device to stay organized. I'm a task management crazy person and love making lists. I, like many before me, have been on a search for the best task management application out there. I've tried a bunch of software and have found very few that I actually enjoy using. Over the last year I have purchased Things and TheHitList and have gone off and on with both apps. I recently took a new app for a spin that has really caught my attention. It is made by the same firm that makes my favorite writing software, Writeroom, and it is called Taskpaper. Now I'm in a jam.

All of these apps have great feature sets and their own perks and pitfalls. With the arrival of my iPad, an accompanying mobile app is a must for any task management system I decide on using and I really want to settle on one. Unfortunately, TheHitList (THL) has no iPhone or iPad app so I'm going to have to let that one go. I really like the keyboard integration in THL and the built in task timer is a feature I wish other apps would implement. Development on the software has kind of stalled and I'm not too confident that the app will live long into the future. I hope so and I'm going to keep tabs on it but I have to now turn my attention to the other contenders.

Things is a superbly programmed application and has a UI that is a joy to use. Whether it's project support, recurring tasks, team members, areas of responsibility or one of the myriad other awesome features of this app, I've been hard pressed to find another app that offers so much in such an easy to use manner. In the name of full disclosure, I did acquire both THL and Things through bundled software purchases so I ended up paying less than sticker price for both apps. I've been using Things for a few months straight and have really begun to depend on it. The Things iPad app is yet another example of Cultured Code's ability to craft a beautiful and useful software experience. The only issue I have is that the iPad version of Things is $19.99 which is twice as expensive than any other app I've even considered buying for iPad. Also, the iPhone version is only $9.99 which, although I don't have any experience using it, I do wonder how the iPad apps differs enough to justify charging twice as much for it. It does sync over WiFi with the desktop app and has all of the same features so my usage wouldn't change cross-platform wise.

Now Taskpaper is a bit different than THL and Things in that it is a much simpler and minimal interface. Projects, tasks, tags and notes are entered using a super simple text formatting trick. Any line ending with a colon automagically turns into a project. Any line starting with a dash followed by a space turns into a task. Any word preceded by an @ symbol is a tag. Anything else is a note. Simple, easy and fast. The other thing I like here that Things does not offer is projects within projects. This really allows a project to be broken down much more granularly. Taskpaper files are just text files so they are easily portable and storable. Using the free service SimpleText I can sync both my Writeroom files and Taskpaper files online and access them from anywhere. The iPad app is the exact same interface so again, usage across platform remains the same. At $9.99 it is half the price of Things for iPad. The only problem? I don't actually own Taskpaper yet and in order to use it after the demo period is up I will need to lay out the $29.99 for the desktop version. This is still much less than the full price version of Things ($49.95) and iPad app ($19.99) but, since I got my copy in a bundle this comparison doesn't work in the real world.

I have a feeling that I'll end up going with Things in the meantime since the initial cash investment is about all I can afford at the moment. Although, when that iPad version of Writeroom comes out, I might need to re-visit the issue then. Any thoughts or tips?