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I am trying to construct a sentence for a printed document that requires an odd usage of a noun that can be singular or plural but is also possessive.

Here is an example of a sentence that contains a noun that could be singular or plural and so both are listed:

Each person selects which task or tasks they would like to complete.

Some people would use task(s) instead of task or tasks. But this is a different issue. I tend to avoid this.

Suppose a related sentence now mentions something belonging to each task. Perhaps a single task is selected at random, we could say the following:

The random number generator decides which single task's requirements are fulfilled.

Here we talk about requirements belonging to one task. But if there is more than one task then we would need to move the apostrophe to after the s. Right?

The list of two or more random numbers decides which tasks' requirements are fulfilled.

Now here is my dilemma, I need to talk about a list of tasks that could contain a single item. Is it appropriate to use the plural?

The list of one or more random numbers decides which ?????? requirements are fulfilled.

I'd like to avoid using something like the following which appears to me as if it is technically correct but sounds wrong:

The list of one or more random numbers decides which task's or tasks' requirements are fulfilled.

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    Real (spoken) English is simply unable to convey the possible distinction in your final example. In the unlikely event that it actually mattered to the audience that only one task's requirements might be met, it would be necessary to opt for different and more explicit phrasing, such as ...decides which of the tasks has its requirements fulfilled. It's just silly to take refuge in a supposedly disambiguating orthography that's incapable of being conveyed in speech, for such a trivial distinction.
    – FumbleFingers
    Commented Dec 29, 2015 at 14:09
  • @FumbleFingers It does matter to the audience in this case as it is for a technical specification that must not be misinterpreted. I will reword the sentence as you suggested.
    – Lex
    Commented Dec 29, 2015 at 15:05
  • DanJAB: If you're particularly concerned that your text must not be misinterpreted, there might be other potentially more serious ambiguities. For example, unless your context makes it absolutely clear what are fulfilled means, that might be a problem. I've no idea whether you're talking about requirements (of one or more tasks) that are actually fulfilled (a statement of fact), or are to be fulfilled (a statement of future plans).
    – FumbleFingers
    Commented Dec 29, 2015 at 16:11
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    Though 'The list of one or more random numbers decides which task's or tasks' requirements are fulfilled.' is precisionist, 'The list of one or more random numbers decides which tasks' requirements are fulfilled.' would almost certainly not cause consternation if it turned out that only 1 task (or even no tasks) had their requirements fulfilled.
    – Edwin Ashworth
    Commented Dec 29, 2015 at 17:08
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    You need to reword this: “Each person selects one or more tasks to be worked. For each task selected, a random number is generated to determine which of that task’s requirements are to be implemented.” ...
    – Jim
    Commented Dec 29, 2015 at 18:28

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I think you should just use the plural which tasks'. Using a plural doesn't always mean that there will be more than one of the item. It's often used when this is just a possibility. For instance, if you said

We'll give out prizes to all the people who show up.

you would not be considered incorrect if only one person shows up (at least not grammatically -- you might still have a marketing problem).

In your case, since you specify one of more at the beginning, and that these correspond directly to the tasks, it's clear that the number of tasks can be one of more.

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