The opening contract/tutorial imposes upon you the obligations of hiring 3 more troops and visiting (and purchasing stuff from) a specific settlement.
To fulfil these terms, you don’t technically need to visit the specified settlement at all. If you’ve already hired at least 3 troops and bought some weapons/armour from a different settlement, the terms of the contract become fulfilled and the contract specification changes to “return to XXX etc.” before you even reach the settlement that was specified.
Conversely, if you’ve already visited and bought stuff from the specified settlement, but have not yet hired enough new troops, the contract continues to specify that you need to visit the same settlement (giving the impression that all the troops/equipment need to be purchased there and not elsewhere).
Also, once you’re familiar with the game, you know perfectly well that better/cheaper recruits and/or equipment may well be available at other settlements that are quite close by. Sometimes, the specified settlement doesn’t even have much on offer at all (e.g. just some rags, broken pitchforks and the odd peddler).
I really think the opening contract/tutorial should be more flexible – e.g.:
— Visit larger nearby settlements (and/or small settlements that have an iron/copper mine, ore smelter, leather tanner, workshop etc. in the vicinity)
— Recruit an unspecified number of troops (however many you want or can afford)
And then it becomes fulfilled when you’ve visited at least two settlements (since it’s always a good idea to compare what’s on offer), bought some weapons and equipment at either or both, and made at least one recruit.