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Losing this much money out of your pocket is easy when running home.

Reduced adverbial clauses need to modify the subject of the main clause to which it is attached (according to what I've read and know).

Does this mean the above sentence is ungrammatical? Is it perhaps ungrammatical, yet acceptable, due to its lucidity and natural-sounding flow?

Thank you
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English 1b3 Losing this much money out of your pocket is easy when running home.
My enthusiasm is dampened more by the unlikely scenario than by the grammar.

I'm quite comfortable with "Losing money out of your pocket would be quite easy while running."

I don't think this change effects the grammar from the point of view of your question, and I see absolutely no problem with it. Emotion: shake

Edit. "Unlikely scenario" is a bit harsh. It just seems unlikely that a native speaker would put it quite that way. Emotion: smile

Did you mean to imply that the large amount (physically, not monitarily) was the reason for the loss??

Is "home" important to your grammar point?

If you stick a big wad of loose bills in your pocket when you go running, you're asking for trouble. Losing that money would be easy while running [home].
Comments  
I find this sentence tolerable without being overly enthusiastic about it.

It would in my view be better as "when you are running home".
 Avangi's reply was promoted to an answer.