Hello Christina,
It sounds like you're holding it together like the champion!
Ugh, a second surgery, and having a port put in while you're still healing from it - what a pain. At least it sounds like you're getting 4 weeks separation between rounds, that's going to be far more comfortable for you.
Heads up that your hair won't likely just fall out like an animal sheds, it can be extremely irritating - itchy, rashy, blistery etc. It might come out very slowly or comically fast, it may fall out altogether or just thin all over. Go with your gut and take the shave when you feel it's time. Personally, if I could go back knowing what I know now I'd have shaved it all of the second it started to fall and the irritation set in just so I could keep it clean and moisturised from the onset.
Absolute best of luck for a smooth first round.
xo Rebecca.