I don't see what there is to fear. If you politely ask for something, the worst that can happen is that they politely decline. When that happens, I just thank them for trying and move on.

The only time I press matters is when a hotel tries to take back something they've already promised. One time I confirmed an extra bed four months in advance at this hotel, only to be told at check-in that they couldn't supply it. It took polite escalations to the GM and social media channels, but I did get my bed, and also comped for my trouble.

So long as I am polite, I don't feel that I am bothering anybody, just asking them to do their jobs.