Interesting points.
1) Lived in Hawai'i for about 2 years. There it's mauka/makai. And/or windward/leeward. Mauka is inland--towards the mountains. Makai is towards the ocean. Windward is North and/or East. Wetter. Greener. The Road to Hana. Leeward is sunny and dry. Waikiki. Diamond Head.
2) I'll probably never do it myself, but I'm definitely at the age where I get Earnest Hemingway and Hunter S. Thompson. I understand that moment when you wake up and say "Well, shit. I've done everything great that I'll ever do. It's all downhill from here. Time to go out with a bang.
2a) In retrospect, when my Dad was dying of cancer, he was trying to end it with a morphine overdose. And the hospice people really didn't care. But I was a good OCD of German heritage, so if someone tells you how much morphine a person can take and gives you a log to track it--even if they literally say "it isn't a big deal if the log isn't completely accurate," you do what you were told, not what the wink and a nudge were about.