Gameshare question??

Okay i have a mini issue and im hoping someone can help me out. I recently bought madden 13 from the PS Store. I gave my friend my info so he could download it and play against me. That all works perfect. My user id is obviously on his system.

My other friend downloaded nhl 13 from the store an this same friend thay downloaded madden from me also downloaded nhl from this other friend with no issues.
I tried to download it but it wouldnt work. Is that because my friend that got madden from me beat me to the download from our other friend?
I get the error message about 2 ps3 systems being active already.

Now i have several other user names on my ps3 that i created just to play other games incognito so people on my original friends list wouldnt bother me.
Should i delete these other accounts and deactivate them them remove or does it not matter since they are originally from my ps3?
Reason being is my friend who bought nhl from the store just downloaded mlb the show and he said i can download it from him.

So will i be able to download mlb the show from him since he hasnt let anyone else download it yet?

Thanks guys!!!