At What Point is the Needle Damaging Records?

You are a little overdue, the damage might've been done already, hopefuly not.
Of course, the needle always damages records but let's not take this subject to the extreme.

Have you examined the stylus with a loop or magnifying glass. Perhaps you simply need to adjust VTF/VTA. I have my catridge (Transfiguration Temper W) more than 5 years and listen nearly as often as you do and highs are as sparkling as when I first installed it.

It may not be stylus wear but rather the suspension giving way. I don't know how to check that, but I agree with Stew, check the VTF/VTA first.

Get a loupe or magnifier and carefully examine the stylus. Sometimes you'll find dirt is the issue. A layer of grunge may have built up that does not come off with normal light brushing.

It may be difficult for an untrained eye to spot mild wear, but it's still a pretty good habit to visually check the stylus periodically.