Sharing folders across multiple Macs

Other than an old post about now-defunct iDisk, I don't seem to easily find an answer to this on the boards so am posting my own question.
I have two Macs – an old MBPro and a newer iMac. The laptop cannot run Mountain Lion as it's too old; both devices now run Lion. Now I want to solve document sharing issues so I don't have to manually manage synchonization.
I want the content of certain folders on my iMac to be available to both devices (and preferable my iPad/iPhone as well) anywhere I go and have Internet access. Lacking Internet access, I want the last synced version available, and when I'm online again, any changes will be synced back to the cloud.
I have iCloud service (25GB for $40/year) as well as 100GB Dropbox subscription that costs me $120/year.  I don't think I need both(?)  Using more iCloud storage means that I'd pay $100/year for just 50GB.  So it seems Dropbox is the better deal at least space-for-money-wise.  The initial folder I want to share is about 7GB but I can see this growing as I sync more things.
I cannot see using simple file sharing from the iMac as it isn't always running; that is, it might be asleep or even powered off.
Anyone willing to share the "best practice" approach to getting this done in a secure way that doesn't have me worrying about some third-party accessing all the documents?
Thank you in advance.

You can use Sugarsync for this, it is free (up to 5GB) and inexpensive if 5G is insufficient.
Once installed you can choose any combination of folders from one machine for replication on another. Changes made on either machine are reflected on the other. It will work on Macs, PC's IOS and Android devices.

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