Just got this bow, a 57' Bear Kodiak.
Both tips have old repairs that frankly weren't done the best.
The pics will show what both tips are like.
https://i.postimg.cc/x8HgGjhg/7661-BCB2-6-E35-4364-8-A96-53-F751-CC31-E0.jpg

I can easily fit my finger nail under the tip overlay so I'm wondering if I could cleanly disconnect the overlay then lightly sand of the old glue and re-apply with some smooth-on, or will I just end up breaking the tip overlays.

https://i.postimg.cc/V62Db0Gd/0-DDFBB40-F980-40-D9-83-A5-0385-DFCB1-D73.jpg

Upon further inspection and thought I believe it may be a better option to buy some Bow-Tuff tip overlays and replace the originals. Any thoughts?

I would use phenolic instead of glass . The glass with the woven scrim isn't made anymore. You can't tell the diff on color glass . I think phenolic is a bit tougher than glass , it's a little harder to sand tho

Yep.  I vote for replacing with new material.  Old ones will be easy to get off. 

I commend you for your skill if you can fix it yourself.  I would contact Bow Hospital at Elk Ridge Archery.

Thanks all for the replies.
I went and ordered both bo-tuff and phenolic tip overlay materials.
It was fairly cheap and I'd like to do another bow if this on turns out okay. Seems I have an addiction to collecting the 50's style bows so there will be more.

So this was my first attempt at tip overlays, Certainly not perfect but it's serviceable.

I took the bulk off with a Dremel then used some small fine files to get the shape, then sandpaper from there.

This bow is a definite knock around bow and not a display piece so I am not after perfection. The previous tips were just not going to cut it though and needed to be replaced.
Initial shaping;


Then some finer lines;

After looking at the picture below I can see now that I could have used more sanding on the second white laminate on the left side to straighten up the lines a bit.

I'm not concerned about the sanding marks on the limbs so much, I think I might just turn this into my first bow restoration project over the winter months.