Are constructs using a slash combined with a hyphen to switch a prefix such as in "on-/offline" as a short-form of "online/offline" (or rather "on-line/off-line") which again stands for "online or offline" (which could be written as "on- or offline") something a native English speaker reader would understand right away?
Answer
It would be understood. However, this is a style issue. There are style manuals one may follow. I use the Chicago Manual of Style.
In formal writing, slashes and parentheses are frowned on; such as 24/7, (s)he, he/she, and/or and on/offline.
However, things having slashes or parentheses as a convention are alright: on/off switch, fractions, area codes, interpolations, etc.
Sentences with examples similar to yours should be rewritten to retain meaning. An additional problem is non-native speakers could be confused.
Try,
I am going online and offline as soon as I get home and find out where I'm at.
Documents can be printed either online or offline.
However, in less formal writing, you don't have to be too careful with style as long as your target audience understands your message.
Still, because online and offline are not hyphenated in modern dictionaries, you wouldn't hyphenate in your construction.
off/online or on/offline are accepted, but on-/offline looks awkward to me. A construction where the words in question would normally be hyphenated would be an exception: para-/ortho-oxygenated side chains
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