Can I player who failed grades, fail again the next go around and still be ineligible? I thought this was not possible but one of my player is about to fail 2x in a row, looking at his newest midterm report. 

Yes, it's a very real possibility to fail both semesters. The only time it won't happen is if a player fails the 2nd grading period. When that happens, he goes to summer school and is back to being eligible the following season.

This is what I have at midterm:

o	Student Name	Yr.	Mid-Term GPA	Cumulative GPA	o
o	Stevenson, Joseph	Sr.	3.0	2.6	o
o	Durazo, Todd	Jr.	2.2	2.8	o
o	Roberts, Bruce	So.	2.7	2.6	o
o	Park, John	Fr.	1.1	2.6	o
o	Shannon, Jerry	Fr.	2.7	2.8	o
o	Woodard, Samuel	So.	2.9	3.0	o
o	Thompson, Gilbert	Fr.	2.2	2.8	o
o	Curran, Antonio	Jr.	3.1	3.2	o
o	Nadler, Jim	Fr.	2.6	2.2	o
o	Tartt, Bryan	Fr.	2.2	3.0	o
o	Montgomery, Michael	Sr.	3.0	2.7	o
o	Swanson, William	Fr.	1.5	1.9	o

Swanson is currently ineligible because he got a 1.9 last semester. So it's possible for him to fail against and miss another 12 games? And about John Park, he's a RS with a 2.06 HS GPA. At 12min, he pulled in a 2.6 first semester. I dropped it to 8 and he's now at 1.1. Any chance he will break 2.0 (so getting a 2.9 in the 2nd half of the semester) with 25min? He's a RS so maybe I should just let him fail and use all the min into actual practice?

I had a player who got a 2.9 first semester, so I bumped his minutes down from 8 to 5 and he has a 1.0 at midterms. Infuriating.