So without going into all the details, is it possible to generalize whether more phono gain creates more dynamic headroom, less dynamic headroom, or the same dynamic headroom?
Without going into all the details, you say? Okay.
You're talking about several different things that are sort of related, but not really.
Gain is simply a multiplication factor. Its usually measured in dB and you can think of it as whatever comes in at XdB comes out at 45+XdB. Like that.
Dynamic headroom, you inadvertently brought up headroom which is a completely different thing altogether. What you probably meant is dynamic range. Headroom is the ability to briefly go beyond a normal range. Dynamic range is the difference between the loudest and quietest parts.
In practice, and without going into too much detail, what you really care about is making sure the phono stage has enough gain to provide your preamp with a decent line level with your given cartridge. You also want to make sure your cartridge doesn't have so much output it will overload your phono stage. Anywhere in between those two extremes and you will generally be fine.