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My personal experience, I didn't set up a trade port until year 8, and I know either year 9 or by year 10 I got my first boat to arrive. At that time, you will have options to set up an order, but each trader has different stuff they can bring next time, so you will end up with a rotation of different goods available.
I think it was 3-5 years from time I ordered sheep to the time that specific trader showed up again with them, it fluxuates a bit.
Merchants show up regardless of the post being manned or not.
On my 2nd town, I had a seeds merchant arrive. I traded some seeds and then placed a custom order for some more, 10 years passed and the guy had not shown his face again to bring me my custom order. Makes me wonder if the feature is bugged.
BTW on my current town, I opened a trading post very soon but didnt fill it with anything because of how long it takes for traders to arrive. And then almost instantly a trader with 2 SHEEPS arrived, and I couldn't buy a single one because I didnt had enough times to stock to make a fair trade. So op, always keep the post stocked. You dont need to have somebody working there all the time, you can just set the trader, stock the post, and then lay him off and hire him again when the boat arrives. They last long enough for the guy to arrive at work.
While the trader boat is there, he will stay as long as you have the trading window open. So next time that happens, just click the thumbtack button to lock the window open, assign a few more traders to work and add the items you want stocked to the inventory window. Once they stock it, trade for your items.