The biggest issue that I see is that the more time he spends dealing with the day to day running of the military is time he isn't spending up shoring up allies in Congress, or rallying governors to keep recruitment up, or stepping into negotiations with foreign diplomats, or even just dealing with the normal correspondence of the day. If he goes into the field with them, he'll be basically abandoning the job of President to others while he is off being a general. Winning the military battles while losing the diplomatic war could be just as damaging as what had him frustrated to start with.
 
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