There's enough conflicting stuff above that it might help to go through some of it.
It is my understanding that the S/H cannot make a "gift" to an employee; correct? . Correct in almost all cases. If, for instance, the employee happens to be s/h's child, maybe not. I'll assume there's no gift.
And IRS will consider this comp to that manager/recipient.. I agree.
Soo once a FMV is established;
the current S/H walks away
with a gain or loss on their shares transferred? . No, not how it works.
Yes, current s/h is selling his stock,or redeeming them to the corp.. I disagree.
On the books the Common stock is $68K and total RE is approx. $81K including CS.
. OK, so only $13k in retained earnings (which for simplicity I'll assume is same amount as accumulated E&P). And let's also assume FMV of the C corp. is $100k. And that his tax basis in the stock is $68k.
Please tell us your understanding of the taxation of this "gift" to all parties, i.e., present stockholder, employee, and C corp.
Is there another way to structure this as a "transfer" of all stock without
tax ramifications to employee?
Don't think so, but if we keep exploring the facts a bit more, we may get some tax back at some level.