This idea that you can overwind a watch is first of all pointless on any automatic watch because the mainspring is not held solid to the barrel.
In your case however it is not an automatic and there is going to be an end of the mainspring that abuts the inner wall of the spring barrel. If the spring is in good condition winding it will not break it, and normally it is not possible to over wind a watch. It is kind of an old wives tale. That for some reason persists no matter what.
When fully wound a non automatic mechanical watch will suddenly get tight at the crown. When you get to that point you can stop. You should not be able to physically wind it any further because you have coiled the spring as tightly as it can physically go inside the spring barrel that contains it, and winding it further if that were even possible would do nothing.
Many higher grade old watches that were manual wind only like this watch you posted most likely is would have had what is called stopwork, it is basically a Geneva wheel mechanism that can rotate through only so many turns and then it physically blocks the object from turning further.
My advice is don’t wind this watch. It has probably not seen service in a long time and the mainspring is probably not modern white alloy spring material and has probably rusted or permanently weakened and might break. If it does break, unless it is a fusee watch, nothing spectacularly bad will happen because the spring will just stay inside of the going barrel when it breaks and there will just be no power transmission.
If it is a very thick pocket watch over half an inch thick, it may be a fusee watch (they were usually thicker, though not always), in which case if the spring breaks because you decide to go to wind it, very bad things would happen. A fusee watch uses a tiny bicycle chain wrapped around the actual fusee cone as part of the transmission of power, and if the spring breaks in that, it can snap the chain or the chain can snap if it is not serviced and then whip around in the watch and usually wipeout some of the parts like the gear teeth or some of the escapement.
Basically the older the watch the more dangerous it is to wind it without knowing its condition inside.
It is possible that this watch you have pictured is a fusee watch. There are not many watchmakers who touch such things. It is the watch equivalent of working on a Stanley Steemer rather than even a Model T- not only very old, but not simple at all, and a lot can go wrong quickly. It takes special knowledge and training to work on stuff like that and it costs money on top of a normal service when you do find someone who can work on them. Parts usually have to be made from scratch to fix them.
My advice is put it in a case and look at it. Just look at it🍌 If you want it to run it will probably need a modern mainspring retrofitted and a modern service which will not be cheap.
Your last question- that’s exactly correct. You would need to set the hands on every dial to the exact time they are in relation to each other and that would be done by pressing the hands on very carefully in exactly the right position at service. The central gear I mentioned called a cannon pinion has a friction clutch on its fit that would allow the setting of time of all of them simultaneously through 1 position of the crown or the lever if it is a lever set watch (a tiny lever pulls out from the side of the face or case). Unless someone put one of the hands on not correctly tight there is no reason that any of them would ever become misaligned in the first place, at least to the others, so you could fix the time just by setting the watch correctly.
Hope that helps. Check the AWCI website and the find a professional link to find a working watchmaker in your area, even if you do not get someone who can help you they will probably refer you to someone they know of who can.
