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I think I could manage the two databases just using the formatted emails to add items to the remote location. Since I won't actually be modifying remote items very often (rare enough that I could use remote desktop to do it when necessary), and I won't generally be able to perform tasks from one general context while in the other (the odd non-online shopping trip aside), that two databases might be OK.

I've already set up an auxiliary table in my Filemaker Pro system at work to manage my most common projects and contexts that exist in OF on an ongoing basis. The scripts in the system send tasks to OF automatically with data from the filemaker database. Of course right now this only goes one way. If I took the time to learn some applescript, I could keep the projects and contexts synchronized between OF and FMP.