the check while running stick is so you can check while running:eyebrows: Nice when you have to pony start it if you shut it down to check the oil, or for gensets, marine engines etc that may run for days on end without stopping. If you want, you can make a mark at the full while stopped point. Most folks just check it to see if there's some in there before they start it and then check it again while it's warming up and add some if needed. The 48A we have had such bad blowby when we got it, you could never get any oil into it with the engine running. It would blow it back all over you. It's been overhauled now and it is easy to add oil without taking a shower.
I'm no expert on the winch, but I would probably unwind enough of it off the spool just slipping it around and around until you get some to connect it to a tree or some other heavy item and then drive away to spool it off and probably polish up the brake surfaces. I always wanted to have a towing winch on a dozer here. Had one on an old 9U for a little while, but that tractor seldom used and got where it didn't run, so it got scrapped. I should have flung a fit to keep the winch, but it went too. Not long after, we got our "good" 9U stuck and couldn't get it out with a modern D5 that was working nearby. Had to have a D7 with a winch hauled in and get it the next day.
There's no comparison between what a winch will pull and what the tractor will pull! The D7 spooled out some cable and we hooked it on. He tried to drive away with it, but the 9U was buried from the D5 trying to nudge it out. (worked about like screwing it into the ground). So the D7 guy held the brakes and engaged the winch and out we came.. I popped the clutch in and cranked the 9U as soon as the tracks hit solid ground and we were back in business.
D2-5J's, D6-9U's, D318 and D333 power units, 12E-99E grader, 922B & 944A wheel loaders, D330C generator set, DW20 water tanker and a bunch of Jersey cows to take care of in my spare time😄