Rob, along the lines of cloud storage, something that would be really nice and help is a change on how Hero Labs deals with Portfolio's.
If you could add the concept of a "character" file (as in a single hero) and allow Portfolio's to "link" to that hero file (maybe in read only mode only or a choice), it would make things a lot easier.
As a GM, I could then have a shared network folder (or cloud solution) where each PC can own their own "hero" file and my portfolio would show those hero's, but i would not have to delete and re-import their characters from their portfolio everytime they made a change.
As it stands now, having multiple people share the same portfolio for editing is proving to be an issue.
-Jamz
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