Sounds good

If it's easier for you I'd suggest simplifying the start price to be either 'close on last trading day of year' or 'first trade of year' no matter when selection was made.

The first trade after posting option seems like it just adds complications

What ever makes it simplest and most enjoyable for you gets my thumbs up!

Great comp even when my picks have me battling it out in Shrewdy's neck of the woods!