The difference in size of the letter "S’ seems to be due to the font. I checked with a few fonts and found that all of the curved letters (C, O, Q, …) did the same thing. I looked at text in an editor and a vector graphics program , and the same thing happens there. This seems to be an attribute of the font design, and not of Blender’s use of it. Using a separate Text object with a very slightly smaller size would even the height out.
To be honest, I do not know why the Text object allows for the Remesh modifier as it accomplishes nothing. The Boolean and Remesh modifiers work with vertices. Text has no vertices to work with, so you need to convert it to a mesh for a Boolean operation.
As for contacting Blender with a special request, it is not really possible. This is open source software, so Blender does not have a “customer service” department, but instead relies on the community to provide support.If this were a bug, they would deal with it once reported, but it is not a bug. On the other hand, if you donated a sizable amount of money to the Blender Foundation, they would be more likely to hear you
Also, here is a link to some tips for using boolean with converted text: