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I would like to keep all my files (i.e. pages/numbers/keynote) automatically synced between my iMac and MacBook Pro. Is this possible? I don't want to have to save something in the cloud each time, then download it from the cloud on the other machine to work on and then save back in the cloud again. I just want to be able to open up either machine and have all identical files there automatically. Is this a pipe dream?

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If iCloud Drive (FAQ) isn't syncing fast enough for you (or you're not on El Capitan ) then you could try a commercial solution (per Gb most are cheaper) or you could use one of the "roll-you-own" solutions.

There are multiple commercial solutions that do this, in no particular order:

Then there's a range of self-hosted solutions which let you use your own network, servers etc to provide cloud storage & sync.

Of course if you put your laptop to sleep if will always have sync changes from your desktop when it wakes up no matter what solution you use.

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