IMO, ask for the company's SOC-2 once you've demonstrated that you are a legitimate prospective customer with a budget and not a competitor or social engineer.
That should address most concerns, or at least make the questions more salient, and it has the added benefit of being vetted by a third party.
If they don't have one, then proceed with the dumb questions, but as you quite correctly point out, no one should be surprised if some questions are rebuffed.
IMO, ask for the company's SOC-2 once you've demonstrated that you are a legitimate prospective customer with a budget and not a competitor or social engineer.
That should address most concerns, or at least make the questions more salient, and it has the added benefit of being vetted by a third party.
If they don't have one, then proceed with the dumb questions, but as you quite correctly point out, no one should be surprised if some questions are rebuffed.