My "Online Local" Aperture Vault is currently 75 GB. The EOS 7D pictures are 10MB each. I spend a _lot_ of time deleting/moving photos offline, but the CF Flash I put in my camera is 64 GB, So just filling that one up (which I can do in a weekend, without much trouble) would be half of my Aperture Photo collection. Aperture has the ability to store your photos "Offline" on a secondary storage - which is where the majority of my photos are (only thumbnails are kept local)
I've taken some 2 GB Videos with my iPhone. Having a Video SD Card is nice.
VMware Images - at 20+ GB a pop, they start to add up very quickly. And, you rarely need them in your system.
256 GB is painfully small. 512 GB would be filled up quickly. I could probably get by with 1 TB, with the 3TB Drive on my desk to shuffle off less frequently viewed Video seasons.
The nice thing about SD/USB Flash drives is you can stick them into your laptop, _and leave them there_ without having to futz around with a cable and a separate spinning hard drive. Then, when you don't need the photos/VMware/Video/TV Season - you just swap another one in.
I'd love to have a 128 GB _Fast_ USB Flash drive - those would be awesome.