You should start the generator once a month and run it under load for 40 minutes to an hour. You could start it first, and turn on the block heater for the load, and then run the big diesel once the block heater has warmed up the block.
I have an '82, and when it is very cold the passenger rear sits a little low too. Don't think it will cause a problem, but like you, I need to get the leak fixed....haha! As long as it is warm it seems to stay level.
Sounds like everything else is under control.
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