How can one tell when they should expect a players second injury recover bump?

Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Tony Martinez

You're not getting one.  Not sure why.    If a player has a 22 day injury and you place him on the 60, you'll get one around day 21 and a second about day 59. 

Dang.  Not what I was wanting to hear but I guess it is what it is.  I guess ill leave him on as long as possible and cross my fingers.  Thanks

You won't get one.   He already has a regular season progression marker.    That's how I know you won't get one. 

Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Ellie Harris
or
Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Kyle Anderson

This guy should get another at 11 AM cycle:
Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: George Ford

Hmm very interesting.  First time Ive ran across it.

Is it just random luck on which players get the extra bumps?  I have 20/20 training/medical and have a guy who I placed on the 60 Day DL with a 176 day injury quite awhile ago and he hasn't recovered at all yet.

No.   In that case, you should get one around the 59 day point and another, if the first isn't too late in the season, just before the season ends.    For the most part, if you're past the A/S break and get a major injury like that, you'll only get one. 

It's been 99 days since Midre Barrios  http://www.whatifsports.com/HBD/Pages/Popups/PlayerProfile.aspx?pid=5355143 went on the DL without recovery.  We're about twelve days past the All-Star break at this point.  Did I screw this up by dropping him to AAA after his injury?

Maybe.  You altered the process when you demoted him.    Not 100% sure though.

That said, they may have changed the program.   Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: George Ford didn't get his 2nd bump two days ago like I expected. 

Then there's this:
Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Roger Hosmer

that's amazing

Wow!

Posted by camden68 on 12/13/2013 10:29:00 AM (view original):
Then there's this:
Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Roger Hosmer

I want this

Posted by brianp87 on 12/13/2013 12:26:00 PM (view original):

Posted by camden68 on 12/13/2013 10:29:00 AM (view original):
Then there's this:
Hardball Dynasty – Fantasy Baseball Sim Games - Player Profile: Roger Hosmer

I want this

Those take a perfect storm (he's my guy).
You need to have $20 mill in medical to take full advantage.
He needs to have a very long-term injury (Hosmer's was ~365 Days).
The injury needs to occur later in the season and carry over to the next season.  In the first season, all he gets is an end of year recovery boost, but in the second year, he gets one after Spring Training and then on the "regular schedule" until he is fully healed.  The "regular schedule" is about every 10 to 11 RL days (that is how long you will have between your two injury recovery boosts if they all happen in the 1st season, after he is actually over the injury.  I think Hosmer's went about 90-100 days into this season, so he got 1 boost last season and just eeked out 4 this season.