Had to start bike, wait, check oil, add more. Did that 5 times it was a half quart low.
Your battery didn't die, you killed it.
A battery has two, maybe three starts in it, then the state of charge is too low to safely start it again until it is charged. I'm guessing by the fifth start the starter was dragging.
Conventional batteries will not tolerate a deep discharge.
I buy cheap, no-name batteries from a local battery wholesaler that deals mostly with commercial customers. They are at least $20 cheaper than Wally and auto stores, sometimes $50 or more. I get 5-6 years out of them, and replace them at the first sign of weakness. Never had one outright fail.
I am diligent about keeping my motorcycle batteries charged, and after killing a few batteries, making sure they are fully charged before starting. A $5 multimeter and a $20 battery maintainer from Menards provide cheap insurance. Much easier to tell if a problem is a failing battery or a faulty charging system.
FWIW, if the battery has enough juice left to run the fuel pump, you may be able to bump-start the bike. Last spring the battery on my FJR (which had given plenty of warning that it was failing, which I ignored) wouldn't crank it, but would run the fuel pump. Fortunately I live on a steep hill. Went for my ride, then replaced it. Quite a PIA, as several pieces of plastic need to be loosened/removed. Be happy the Vee battery is so accessible.