re: Growing hair out for first time. any tips from experience??

One possibility is to let the top more freely grow, while keeping the sides and back at least a little on the short side. Then when your hair gets long enough on top you can start letting the sides & back grow out to match. Depending on what your hair looks like, this can help you navigate some of the awkward phases... and while you're in the process of growing it out, you will most likely experience several awkward phases. Each week your hair grows longer, it's almost like a new haircut and your hair isn't well trained to keep a style at that length; so sometimes it'll look better than others.

I haven't had a proper hair cut in at least three months, so mine is getting a bit long and I'm in a similar place... not sure if I'll just tidy it up now at medium length or let it go a little longer. If I let it go longer, I'm probably going to do what I suggested above.