This is my first season playing HD and I'm a little confused about recruit signing. Can the recruit still sign when he's at " considering you among others" or does he have to be "considering you"? Also if 2 schools are battling, both offer scholarships, and one is ahead of the other at the time recruiting ends, does the recruit sign with the school or does he not sign at all?

The recruit does not have to be considering ONLY you.  He may be considering others and sign with you.  

When the battle is close it will drag on for awhile, but there are some standard times that tie-breakers resolve… for example 11am the day after signings.  I forget when the other tie-breakers occur.  

Pay attention to scholarship messages to know who is in the lead.  Those are the most accurate statements of where you are at with the recruit.  Home visits, etc. will often give very positive reports, and then the scholarship message may be positive, negative or neutral sounding.  The recruit will sign with someone eventually, even if the battle drags on several cycles.  

Welcome to the addiction.

Yes, a recruit can sign when he is considering multiple schools. It most likely won't happen at the beginning of signing though. After signing starts, If one of the schools makes enough of a push and the player's signing threshold drops enough then it will happen. Also, if one of the schools fills their spots then the player will sign with the other school. Otherwise, the decision will be made at the 8am cycle on the final day of recruiting.

Thanks a lot guys

Here's a list of those scholarship messages.

Scholarship messages are the best way of knowing which school is ahead. There is also the word on the street. If it says the player is struggling then the first team listed is ahead.

If you didn't use FSS this recruiting definitely look into using it next time. I would say is a must.