1. Refill the oil, make sure when you replace the oil filter you fill the filter up with the new oil to the top as well. The suggestion is you should run the engine for a few minutes to circulate the new oil prior to putting it up. I'll typically replace the oil and add stabil at the dock to a full tank and then motor over to the launch to cycle everything, then you are good for the winter.
2. Bumping the starter is easiest if you remove the kill switch and then turn the ignition for a second to cycle it.
3. Seems to me that its a personal preference. I never do the bleach but once drained I hook everything back up so as not to lose anything, forget where I stored it, etc. I don't go around huffing ballast bags to worry about breathing in mold spores.
4. Where you're at I'd prob say yes to the anti-freeze but is the boat stored in a heated garage or outdoors unprotected from the elements?