Based on the previous two threads by Ton80.
I decided to do stats for Check-Out to see what value should you bid in total in order to maximize winnings. I used stats for the previous two seasons in order to justify my work.
RLB- Range Lower Bound
RUB- Range Upper Bound
Date Center Range RLB RUB ARP of Prize Offered
1/19/2017.........$15.95 $13.95 $17.95 $9,230
12/28/2016.......$18.95 $16.95 $20.95 $12,381
12/21/2016.......$20.25 $18.25 $22.25 $8,296
11/22/2016.......$17.85 $15.85 $19.85 $16,721
10/31/2016.......$20.06 $18.06 $22.06 $6,879
10/7/2016.........$21.31 $19.31 $23.31 $22,655
6/13/2016.........$18.75 $16.75 $20.75 $10,109
5/27/2016.........$15.95 $13.95 $17.95 $11,765
5/3/2016...........$16.45 $14.45 $18.45 $6,000
4/14/2016.........$20.25 $18.25 $22.25 $6,800
3/2/2016...........$15.25 $13.25 $17.25 $6,337
2/8/2016...........$15.55 $13.55 $17.55 $6,301
1/4/2016...........$17.45 $15.45 $19.45 $10,787
12/18/2015.......$20.45 $18.45 $22.45 $13,158
11/13/2015.......$19.83 $17.83 $21.83 $17,020
10/6/2015.........$18.45 $16.45 $20.45 $9,057
Running through the numbers, just on these alone, you should go either $18.45 or anywhere in between $19.31 to $19.45 to win 11/16 times. Not as sturdy as I hoped, but only 7/16 of these games were won, so you do better than the actual outcome if you went in this range.
I decided to split the data up to 4 digit prizes and 5 digit prizes. For 5 digit prizes, you get a 7/8 shot of winning if you guess in between $19.31-$19.45. For 4 digit prizes, you can't do much better than a 5/8 chance with either $14.45-$17.25 or $18.25-18.45.
EDIT: Added periods to make the graph look better.