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As far as I know, a project resource can't select different roles at timesheet line level. Is there any way to cater a requirement to create timesheet lines for same resource but with two different roles either on same project or on two different projects?
You mentioned correctly that one resource can have a single role assigned only in D365FO, which kind of limits / stops you from achieving what you describe above.
Yet, in my answer to your previous question, I mentioned the possibility to leverage the PowerPlatform for that purpose, which can help you overcome also this issue.
The PowerPlatform is the only alternative that I see as an alternative to making a system modification.
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