So i brought that one black guy the medical kit and all the sudden it says Scoop chance lost and all my uncompleted cases are now expired..
I saved the game to my memory card with everything expired, but I don't know which saved game to play from. has anyone else had this happen?

this is what happens when you dont do the main quest. it just cuts you off. gotta do the main quest and at times, screw saving people.

You were doing the main quest and you were at the part where you save brad with the medecine, right?

It said you finished the case and then it told you the next case starts at 11, you pressed A, then the next case was somehow allready expired, right?

Yeah that actually happened to me too.

I think that the clown bossfight may, for some nonsensical reason, be mandatory. That is the only reason I could find to explain this. I restarted, beat all the main missions as fast as possible, beat the clown, then used the free time to solve scoop missions. I was then able to move on. It may simply be that I didn't beat the mission fast enough first time around.

Either way sorry, you gotta choose to save your progress and start over. On the bright side, you'll be much stronger.

same happened to me, ecpect it was a dude with a shopping cart boos fight, and i couldnt find out how to get into the pharymacy

Yeah after I beat the shit out of that guy I rescued some bitch with a shirt that said 69. (tip: take a close up picture of her thong, its a ton of points) I gave Brad the medicine (forgot his name in first post) and then it said case expired. I guess I'll start over from my memory card save (right before defeating carlito the second time).

same thing happened to me, i do believe you have to have the medicine back to brad before the next case starts. i think it starts at 11, so you have to beat the grocery dude and have the medicine back BEFORE 11...

None of the scoops (Clown included) are mandatory...you might not have made it back in time...

He didnt make it back in time. Now you can focus on saving people and getting the other achievements. Same thing happened to me to. The clown is my favorite psycopath. And when you get his chainsaws they totally own.

The cahinsaws plus the Engineering, Entertainment and Criminal Bio book = best weapon in the game.

I carry those and the Real Mega Buster...and a few health items (books)...that is it.

Heres the deal if your main case is gray it means you already have run out of time, It will still let you complete it but its already to late thats why it fails ya after you complete it. Happend to me once on the girl hunting mission.

So, here is my question about this. If I continue on and save people and do side missions since my case files are expired I can level up and get PP and achievments. BUT when I start over to do the case missions, will all those side missions and survivors pop up again like they were never done? Or will it remember I saved the japanese guys and killed the crazy clown and the dude in Crispin's?

Unfortunately yes. Any achievements will be saved but all the missions reset themselves.