The first scholarship message is obviously a leading message. I believe you will get numerous scholarship messages when trailing, depending on whether you are' trailing, but almost in the lead, dropping off a bit, falling behind, or still being considered, but not really close. The same goes for when you "close the gap".

Billw, you need to tell your friend that when he is in a battle with 2 other schools, he cannot stop putting money into the player and expect to maintain his lead. You also need to tell him that such a small distance advantage is not enough to overcome such a wide prestige gap especially in DI. Please explain to him that he should expect to spend 1.5-2.0 times the amount the other schools put in just to break even.

The 8:01 scholarship message indicated he was in the lead yes but that was just the 1st cycle which doesn't mean diddly. He inevitibly fell behind by 2PM as indicated by the scholarship message and the WOTS response and yet he put no more effort in. The 2AM scholarship message shows that the other school has significantly widened the gap. Duh, they were putting continued effort in. Your friend needs to understand that he is in DI recruiting against experienced vets, not noobs. He should know that he can never assume anything because nothing is in stone until the player is signed.

roughly speaking, I would read the three messages as

1. you are in the lead, but not by much

2. roughly tied

3. trailing

These seem consistent with FSS.  Likely answer is that he stopped effort and others continued.

I think it's to give the coach a heads up that he's falling further and further behind the lead school.  These messages are pretty handy stuff to get actually.

Everything in recruiting translates to point values.  I think there are certain levels where a scholarship email is triggered - say, for instance, if you take a 5 'point' lead in recruiting, you'll get an email saying you're in the lead.  When your friend lost the lead, he got an email (it was close, say it was just a 1 point lead).  When your friend dropped to 5 points down, he got another email.  As he falls further behind (10 points, 15, etc), he gets more emails.

My $.02 on it at least.