Danielle,
I feel like I am going through some of this with him. My free flap surgery was 2/10 and I had a very hard time tolerating the trach. They took it out after the first 3 days and switched me down to the smallest size before transitioning me to 'the button'. I would press on this when I wanted to speak. Otherwise it was neck-fart city! My teach took a long time to close - I was on steroids when I went into surgery (huge mistake in hindsight). Almost 3 weeks. Once I was off the steroids it closed up within 3 days.
With regard to pain meds, I had much the same experience as Vanpaddler - I didn't need a lot of pain meds after returning home, have only used Tylenol and occasionally the hydrocodone (2x but it leaves me with a headache). The one thing they gave me in the hospital that I sorely wish I had now is Ativan - it is an anti-anxiety drug. Calmed me down, helped me relax and sleep. Helped me so much more than the morphine. I actually stopped the morphine 3 days before I left the hospital.
NG vs. PEG: if he's OK with the NG now I guess go with it. However, I agreed to have mine placed while I was in the hospital because I learned I had to go on for rads & chemo, and because I literally felt like a cow with a ring through my nose. Hated it - I was always pulling on it by accident. Plus, not sure I would ever have left the house to go shopping if I still had it. Too hard to explain. The PEG is easy to use, very straight forward. Mine got infected due to the steroids I was on, but most people have no problem with it. Plus I can go out in public and no one is the wiser. No idea what his preference will be.
Continued good healing and prayers to you, your boyfriend and his Mom. I am learning this is a process and we just have to put one foot in front of the other and get through it

Heather