Welcome to Legal English.
Using "should" == "shall" == contractual obligation. It's a legalism. It doesn't lead to "questioning". It marks the sentence as a formal contractual obligation.
Using "would" == "will" == nice idea. It marks the sentence as an optional feature.
Questioning is part of facilitation, organization, helping, building trust. Not a consquence of word choice.
Using a bare verb without the modifier makes the sentence slightly harder to highlight as a formal requirement. And in the case of super-complex verbs, it can get a little dicey to figure out how to conjugate it.
Easy -- verbs like "to notify" or "to create".
The system notifies via email. (The verb "to notify" is conjugated "notifies" for "the system"--whatever that is.)
The system shall notify via email. ("to notify" becomes "shall notify" -- no conjugation. Very simple.)
Hard -- verb phrases like "to log in" or domain-specific verb phrases like "to extract, cleanse, transform, deduplicate and load" or a noun like "prospect" which has been verbed. The longer phrase which has several verbs buried in it is hard to conjugate: conjugate each verb? Or try to conjugate the long phrase as if it was a single word? Since any noun can be verbed in English, it's hard to know how to conjugate those made-up verbs.
The system extract, cleanse, transform, deduplicate and loads when the user clicks enter. (English trivially verbs any noun phrase.) Or is it extracts, cleanses, transforms, deduplicates and loads?
The system should extract, cleanse, transform, deduplicate and load when the user clicks enter. (The hideous phrase is left intact, no mystery about the verb conjugation.)
["What?" you say, "any noun can be verbed in English?". Yes. Any noun. I'm going to stonewall on that. I've often stonewalled on that. Even the specifications should stonewall on that.]