How much flash storage do I need for 13" Air for work/business?

Hello - I have a 2010 15" MBP that I use for home and business, but I've decided a need a lighter, more portable notebook to take to/from the office, on business trips, etc.  I'm not familiar with flash storage, but I've been fairly happy with my current MBP response times.  It has 4GB of storage which is nearly at capacity with my entire iTunes library and a number of movies I have stored on it, but I don't need the MBP optical drive and all of those media files with me when on the road.  I would primarily use my MBA for Keynote or PPT presentations, playing short form video, MS Office and Web access.  I plan to keep my MBP as my main workhorse PC at home for as long as it holds out, and use the 13" Air as a portable notebook.
So... do you think the standard 256 GB of flash storage likely sufficient for me, or should I spend the extra $500 for additional capacity?
And is it reasonable to assume I'll be able to transfer working files easily between my Pro and my Air 2-3x/month via a Thunderbolt/Firewire adapter, or should I just move everything to the Cloud?
Thanks!

As long as you aren't planning on storing a large collection of large movies and you have reasonably sized media (iPhoto/iTunes) libraries, you should have no trouble working with 256GB of storage.
As for transferring things, I would say that anything that is "mission critical" should still be retained (and backed up!!) locally. But for general documents, iCloud and other cloud services (Dropbox, etc.) work just fine (and have the added advantage of making things available to view/edit on mobile devices).
Also, in regard to transferring files, you might want to consider AirDrop, which you can read more about here: http://support.apple.com/kb/PH11376
Hope you enjoy your MacBook Air!

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