I don't know what the problem is here. Shouldn't have lost out in drawing a firearms permit several times in a row unless you are applying in last chance. Get in on first lottery - NOW!
2nd - there is no rifle hunt in IL so you can't use gramp's rifle.
If you are applying for limited hunt areas your chances will be slim but county by county permits? Much, much more likely to get them I have never missed in years and years or applying.
Another question I have is have you taken a hunter safety course?