Hi, Nschacor,
We have an excellent primer covering some of students' most frequent questions about retaking the LSAT here:
https://www.powerscore.com/lsat/help/retake.cfm
In general, retaking the LSAT two or three times will not reflect negatively on your application. It may even indicate that you are especially dedicated and willing to do what it takes to get the score you want for your application. The majority of law schools accept your highest reported score for admissions. You should consult the admissions offices of the schools to which you are applying for school-specific policies and attitudes towards multiple LSAT scores.
For upcoming fall admissions, the February exam is often considered the final LSAT for an admissions cycle. Since there are few likely downsides to taking the test three times instead of two, and since you will miss many important deadlines at some of the schools you wish to apply to, taking the February exam strikes me as a sound decision. You may even achieve the score you need!
If you do wish to retake it in June, be sure to consult the schools you're applying to. Schools occasionally offer conditional admission based on achieving a higher score. It would be better to tie up as many loose ends as you can now in order to keep options open while you prepare for June.
Good luck either way, and please follow up with further questions!
