I don't think you'll have too much of a problem. You can configure the add-in to save its info locally. You can still use rules in outlook, just be careful when applying rules to the folders that the add-in creates to hold its info.
RE: the two computer set-up. This is a challenge that has only partial answers. You can set up the add-in on two computers and use a handheld device to shuttle data between them, but certain changes, like adding a new project name, don't get transferred.
Depending on your degree of need, you could pick one of these other solutions:
1) keep the add-in on your work laptop and take it home when needed.
2) keep the add-in on your work pc and use windows xp's remote desktop connection to let you work on your work pc from home via vpn.
3) keep the add-in on your work pc and just use outlook to view your tasks on your work pc via vpn.
4) keep the add-in on your work pc and usa a PDA to transfer data from work to home. Don't make any changes at home - consider the home pc to be a 'read-only' view of your add-in data.
5) keep the add-in at work and print out copies of your tasks, etc. to take home. Work from the copies and mark them up and enter changes when you get back to work.
I'm sure there are other answers such as using a portable HDD, too.