That's awesome! That's too hard to do!
When I won my biggest HP ever ($5,400), it was the first time EVER in the almost 20 years I've been gambling that I came out ahead for the year. It was only by a few hundred but damn it felt good. Haven't come close to breaking even or coming out ahead since. The life of a gambler...HHH!
Yes. Tedious, but necessary for tax backup. I don't go overboard with detail -- just keep a daily log of how much total I won/lost at each property. I enter this info in the notes section of each trip's calendar event on my iPhone, so I can do it on the spot and all the trip details are in one place.
For properties where I care about keeping track of status, but that don't have a coherent way to check updates online (looking at you, Cosmopolitan), I also take a photo of my beginning and ending point balances each day on the first and last machine I play. Then tally up total trip win/loss, total points (base and multiplier), and coin-in after the trip is over.