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Thanks for the response.

Option #2) I like this option. How many on hold contexts do you have? I am thinking that I would have one corresponding to each Life Area (@Work:On Hold, @Home:On Hold)

The only problem with this is that there is no way to view all on hold items for a given context. So if I am at home on my computer and just want to see if there is anything on hold that maybe i should work on now, i cant really do that. I would have to scan the entire @Home:On Hold context.

Option #3) I agree, I do not like moving start dates around.