I am currently a senior and I took my first ACT and got 27. In June 2015, I managed to pull it up to 31(composite), 33(math), 28(Reading), 30(English). I hoped my final try would be September 2015, but i got the exact same score of 31 (composite):
25 - English
33 - Math
29 - Reading (improvement)
35 - Science (improvement) 
I have to admit, I ran out of time during the English and the reading test. 
So should i take the ACT again in October 2015? (money and colleges accepting scores isn’t an issue) Also, does it look bad if i take 4 ACTs.
No you are not showing improvement in the score, and the superscore is a 32, which is not a bad score.
It depends on the schools you are targeting - you’ll want to look at the freshman scholarships and see if you would qualify for more with a higher score.
My son had a 30 which gave him an excellent scholarship but after his last - and 4th- ACT test he scored a 32 which will provide him with significantly more scholarships.
Best of luck to you!
Your scores aren’t necessarily improving (approximately the same composite, with a different breakdown), so I wouldn’t suggest wasting time and retaking again. Your scores are fine as they are.