Wow, this is perfect and really well laid out. Thank you. That's crazy to think about how much you save if you are over-extending but have the overextension in player salaries that you trained yourself.
In your instance, lets say you're overextended with your current team but are not paying the tax because of what you described. Lets say you add another player with a $30k salary. In what order does the cost basis get calculated? Like lets say you purchased all of your starters for $4k each (20k total for 5 players) and then you add this 6th player for 30k; do you pay the overextension tax now that you have that player on top of your already existing salaries or do you avoid it because your cost basis for your starters is only calculated at $20k total?
This rinse/repeat scenario that you outlined, do a lot of teams do this? How long do you cellar dwell? Also, for trainers, is the expense for an exceptional or world renowned coach worth the benefit?
You're clearly very knowledgeable about all of this so I hope its ok to be picking your brain.