Well, I am afraid that only a person from the Windsor Model Railroad Club will be able to answer that question. There are many different ways and schemes the clubs use to operate with. From your note, I gather that they use some sort of way bill, but that is not helpful without knowing if the waybill is for a load, a car, or a whole train. Are the way bills individual cars or all printed up on a schedule. Then there are other complications like whether their rules state that full cars are supposed to placed in front or behind the existing cars on the siding. The possibilities are almost endless.
They should have a rule book that they give to to read in advance of operating.
Also as you are a new member they should assign someone to work with you on your first few trains and teach you all that stuff. That is what a club is for.
The best way to operate for me is to follow the prototype which means some pre operating secission paperwork but it can be fun. A train arrives at a yard and is broken down into blocks that are destined for certian areas on the layout, if the railroad is small you could form the blocks by industry and put the blocks of cars together in the train as to the industry location on the line. When I operate I find it best to move the model trains as the prototype moves their trains and keep the operating secession as real as possible. Take one more step beyound waybills and form switch lists which are used by prototype crews on local trains to get the right cars to the right customer or industry.
I hate to say this, but you would need to ask a club member. I would ask questions such as “which direction is considered north or west?” and “which track at the paper mill gets empty boxcars for loading?” and “which yard is the (city name) yard?”. I would also ask what town names are, business names (if there is no sign), and any other things that I would need to know to run an operating session. Experienced operators may even need a reminder from time to time. I would expect to have a few questions as an operating session progresses, but you should expect to be reasonably familiar with operations in 2 or 3 sessions. I would think that for a new operator, they would give you a fairly straightforward run for the first couple visits, or possibly even run with a veteran crew member.
If you have run your own layout realistically, such as spotting and picking up cars, running through freights, and so on, then you should have a pretty good idea of what to do.
I wouldn’t hate to offer that advice. Considering that everyone operates probably at least a little differently, I think it’s the best place to go for help. And if nobody in the club is willing to help out a new member, I personally would quit and find a different club!
Again, I could be wrong, but I think the reason for the question is because the OP doesn’t have any operational experience, at least not with the waybill system the club apparently uses.
Well, maybe a little clarification is in order. I didn’t REALLY hate to say to ask a club member, but what I meant was that I was sorry I couldn’t more accurately and specifically answer his question. As far as his experience with a waybill system, well, now that I think about it, I agree with your point. My intent was more along the line of the actual process of moving the train and switching the cars. That could involve (depending on the system used) waybills, car cards, computer generated switch lists, a “loads in, empties out” system, or simply switching random appropriate cars to a destination.
However, he did mention waybills, and I probably should have explained that prototype waybills are the RR equivalent of a trucker’s bill of lading. Generally, a waybill states what the load is, how much there is, what car it’s loaded in (reporting marks and car #), where it came from, and where it’s going. For bulk commodities, such as coal, one waybill could describe the whole train, it could say something like 10,000 tons of (whatever grade) coal, loaded in car numbers (followed by list of cars #'s and initials), where it was loaded, and where it’s going. Waybills can also include any special instructions, such as size or weight restrictions, Haz-Mat info and 24-hour emergency phone #, special routing instructions, empty car return instructions, or nearly anything else that may be needed by train crews. So as it is with the prototype, modelers also use waybills, usually in a simplified format, for similar purposes.