DTNY07
Level 7

I am copying this from The tax advisor.  Line 2 is the reason why I don't think it qualifies.

Meeting the Sec. 1244 Requirements

Second, the stock must be issued in exchange for cash or other property (other than stock and securities) (Sec. 1244(c) (1)(B)). Thus, stock issued in exchange for services does not qualify (Regs. Sec. 1.1244(c)-1(d)(1)). (If possible, the corporation should pay shareholders in cash for services rendered and then permit them to buy the stock, if desired.) Stock issued in exchange for stock or securities, including stock of the issuing corporation, normally does not qualify for Sec. 1244 treatment. However, stock received in (1) certain stock dividend transactions, (2) an E reorganization (a recapitalization) under Sec. 368(a)(1)(E), or (3) an F reorganization (a change in identity, form, or place of organization) under Sec. 368(a) (1)(F) can qualify.

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