Time-sensitive tax questions re: selling shares

Hi Everyone, Thanks for your responses.

@allyphoe
Clarification: I did not yet sell the shares. I’m about to and I need to decide between 1/1/2018 and 1/1/2019.

@thumper1 , Yes, this pertains to me and, yes, I do need to decide before tomorrow. It’s a family business and you can sell the shares effective Jan 1, 2018 as long as both parties agree. My uncle wants the check cut and deposited Dec 31st if we go with a 1/1/2018 redemption date.

The reason any of this is relevant is bc of college financial aid. 2018 is the base year for my 2nd child (two kids will be in college). 2019 is the base year for my third child (three will be in college).

My first child is a freshman in a meets-full-need college right now, so income is highly relevant.

Ultimately I have to decide what is the lesser of the evils: the company reporting (but not distributing to me) income again to my taxes (roughly $5k - $7k) via K-1 form plus the shares showing as an asset, or a larger capital gains event if it all has to hit in 2018.

Thoughts? Thank you