To B.C. or Not to B.C.

First of all, I am not talking about birth control, I am referring to my Big Chop. I haven't done a lone term transition in a couple of years, and that was me primarily just cut my ends and doing two strands. I even wore my hair under my head wrap, which was a blessing more than a curse. I know some people were like why is she always rocking that thing on her head. Well it was either that, or I would have to spend days I was studying to actually do my hair in braids (nope that wasn't going to happen). Now that I am older, I have to make sure that when I go out on assignments, that I my hair looks a certain way aka no head wraps. I tried doing my beloved two strands, and yeah tangly mess is all I get. It's like my ng is fighting with the texturized part. So, my whole thing when should I really just chop my hair? Should I wait until it warms up some more, or when I have at least 4 inches unstretched hair? Right now, my tentative date to chop is July 7th, no real reason behind the date, it just came off the top of my head (like a lot of stuff lol).