There is a trick to using bolts rather than studs and nuts and I find it easier. My tires are loaded and I'll be putting them back on after splitting, same as you.
Start with the hub just a bit low and put one bolt in at 3 o-clock. Now simply raise the jack until you can put the rest in. Way easier than trying to get the wheel and five studs lined up while pushing and lifting the tire.
I bought a valve to fill my tires from Amazon and used RV anti freeze. Just used gravity fill and it worked great. I found a site (googled it) that had a chart for the volume of my tire, pre measured that amount into a five gallon bucket, set the bucket on a ladder and let it drain empty. Might have taken an hour per tire?
EDIT: I just remembered that I cheated a bit because I have a five gallon pail with a spigot at the bottom for running anti freeze into my inboard boat engine. But siphoning still works, just have to fill the hose or suck on it like the old days of getting gas from dad's car to run your toys.
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