What happens to starter brush leads when you don't know when to stop cranking

You have farmland in/near Naperville?
I wish, farmland around here is worth a fortune, because it will eventually be developed.

No, back home where I grew up in Iowa.
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I was taught to only crank so long and give the starter a break for a minute or two. Take that time to figure out why the engine isn't starting.
Maybe prime the engine if it hasn't been started in a while.
I've looked at a wiring schematic of one before and got a headache. Don't know what the point of it all was? My Dad had a 4010 Diesel when I was a teenager. He had our family mechanic who is a pretty sharp guy come over to do something to it and he was pretty dumfounded by it. He was a mechanic in the Air Force with 20 years experience after that by the time I'm thinking he was over so it certainly wasn't his first rodeo with 24 volt systems either.
Yes, with one battery having its negative post grounded and the other battery having its positive post grounded, it can be very confusing. But if you just consider that the chassis of the tractor is being used as a battery cable, it might help to clear things up. One thing to avoid is having any power consumer grounded at all. Very difficult when the vast majority of radios etc. are built negative ground. So, the best solution is what JD did when they put the alternator on the diesels and make it negative ground like 99% of the vehicular electrical systems are.
As to why JD designed an electrical system like that, the only explanation I can think of is to cause the owner to return to JD for service.
We have one of those to this day. Yes, it's a 12 volt system.
Love those tractors.

Any weakness a battery may have will be revealed on a cold day with an old diesel tractor. I remember working on a farm trying to start an old IH 806 in the winter, and my boss never seemed to plug things in... My thinking was if we have block heaters we should use them.