A 2014 20th round becomes a 2015 18th, a 2016th 16th etc. Once the value hits a 2nd round, you can't keep a player further.
The potential reason to slot Reyes/Braun in a lower slot than Stanton/Machado/Bogaerts is length of time one could keep the player, if the player hits. Would keeping a 35 year old Braun as a 12th round pick be worth more than a 29 year old Stanton in the same slot?
Well, you wouldn't have to keep Braun at 35 years old, would you? You could have a different keeper by then... Interesting format though, and I see what you're saying... Stanton would be your best keeper long term because he's so young, so I'd put him in the 20th... Then as you have them... With the bottom two bumped up a slot... So...
Stanton - 20
Bogaerts - 18
Machado - 16
then as you have them...