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Toodledo is a thing in itself. It has a very good web interface but they pretty much left the desktop and mobile integration to others. I have a sneaky suspicion Jake is the only developer so the development priorities are shaped by what he can / want to do, and not necessarily by what makes more sense from the user perspective.

Outlook doesn't have to suck. It's an incredibly flexible tool that can be set up to closely mimic what Toodledo does. I assume you're familiar with setting up custom views ?

What does suck is mobile client integration. Just like Toodledo...

If you can make gSyncit work for you, you should be set.

If not, check out Outlook.com. If you create an Outlook.com account and sync it to Outlook (no special tools required) it will support most of the Outlook task properties such as Start Date and Category. It will also sync them to Apple Reminders. You won't see the Start dates in Reminders, but there are mobile task and calendar apps that can use that data (CalenGoo, PlanBe). So you can use Onenote to track project info, create Outlook tasks, sync them to mobile, and back.

I switched back from this setup to Toodledo because I wanted to use a more advanced task manager (2Do) and it didn't work well with Outlook - it would not sync any special task properties via Reminders. I also grew tired of Onenote, it's a great tool for storing data but hard to keep organized when actively tracking multiple large projects. I am using a mind mapping type software now and it doesn't integrate with Outlook anyway.

But Calengoo<>Reminders<>Outlook.com<>Outlook<>Onenote worked very well for me.