Fact:

Acme corporation (S-corporation) owns real estate and publicly trade security shares

Acme corporation has two shareholders at 50% each (Person A, Person B)

In 2012, Acme corporation purchased stocks in one transaction

4 additional people (People C, D, E and F), not shareholders of Acme corporation, contributed money proportionally (not equally) for the single stock transaction?


Question:

Question #1: We would like to liquidate purchased stocks as early as possible to ripe the gain. What is the best way to handle this transaction to pay minimum amount of tax?

Question #2: Person C, has a large personal capital loss from previous years, how can Person C leverage capital loss from the sale of stock transaction?

Question #3: Can we create a new S corporation, equally own by Person A, B, C, D, E, F, and have Acme corporation to transfer purchased stocks to the new corporation at cost, then sell the shares at market price, then let the income flow through each person’s own 1040?