so i want to know, what is it like playing on Master from start to finish (a metaphorical finish) is it stupidly hard.. do you die all the time, or do you get used to it the more you play?
A mix of both. Sometimes you'll rage at the Bandit Chief that one shotted you, but other times you'll feel a real sense of accomplishment when dealing with Dragons and whatnot. Perseverance is the key here; if you don't get it right the first time, keep trying and modify your strategy until you get it right. Sometimes you'll have to eat your ego and ask for a Mercenary's help.
Oh... and I'd stay away from the Smithing/Alchemy/Enchanting synergy if I were you. They make you a tad too powerful, even on Master (hence losing the whole purpose of playing on that difficulty)