How would you create the hands wrapped around the wheels like in the image at:
Would you use the pen tool?
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With the Pen tool P draw the curve of the hand, and when you get to the end of the fingers, create a corner point by holding down Shift, and the rest is just straight lines
Select All CTRL/CMD+A, then select the Shape Builder Tool Shift+M
Use the shape builder to make the circle one single shape
Using the Direct Selection tool A, select the corner anchor for the finger tip
Click and drag the Corner Widget to make a rounded corner
yes, using the pen tool (as opposed to a freehand drawing tool like Illustrator's pencil) is the best way to approach this type of illustration. Using bezier paths will help you make nice straight lines and well-rounded curves. This tutorial on Adobe will help. This one is good too.
If you are wondering particularly how to come to a point then change the direction of the curve, like at the tip of the fingers, you can do that too by moving the handles of each point. See the illustration called "points on a path" on the first tutorial link I'm sharing.
Obviously you haven't drawn 1000 pairs of hands, so you aren't especially sure how to work this through.
At first you should a little research what makes them hands. Take a selfie or do a web image search for "Binoculars watcher". For selfie you do not need binoculars, a pair of right sized bottles do well.
Place the photo into Illustrator and lock it. Then you take the pen tool,as you already guessed and trace your hands with the needed accuracy. One hand is enough, you can duplicate and LR-reflect the result. You can well simpy click only at first and then round a part of the corners with the anchor type conversion tool.
Insert as few anchors as possible to keep it manageable. It doesn't harm at all if it's clunky, you will soon round everything to the right forms.Too much anchors are practically impossible to get right.
Remember: there's no need to make the hands exactly circular. They can be a little bigger than the wheels and make a contact with the wheel only here and there. Or they can be a little smaller than the wheel (=hold tight)
Not asked: If I try to sketch a hand to your image (it's freehand pencil with mouse, sorry for irregular curves) It would be quite different. That proves you can do nearly arbitary simplifications. Do them, if the wanted appearance needs them