An Update:

So I ordered some silicon mold off Amazon and used them to position over the emblems. I took plenty of photos and measurements, and when applying the mold I tried to adhere it to a part of the car that was fixed that I could use for reference, i.e. around the edge of the door for the 'Cherokee Sport' emblems.

After the molds dried I took them off and used a heat gun/fishing wire that worked pretty well. A few died in the process but I think I'll order one new emblem off eBay that will be enough since the letters are the same. The final step was honestly the hardest and that included stripping the cheap plasti-dip the previous owner put on and the glue left on the back of the emblems. I just used a solvent and towel and worked the glue off with my fingers. It sucked.

My plan is to just put emblem adhesive on them and put them against the car in the molds after it's painted.

See pictures; I'll let you know how it goes!

 

Looks like your idea worked really well so far.
So if understand you correctly probably going to use something like this:


Apply that to each letter in the mold and press the letters back on while in the mold?
Can trim that blue stuff?
Make it straight at the bottom of each emblem?

 

So this has been something that I poked around about here and there for awhile now.
Pretty much how I research all projects that I am thinking of doing. LOL.
Well today I came across this:

https://www.adhesivetemplates.com/

At the top of that page is where you can find the template for the specific application.
This is what came up for my '00:

https://www.adhesivetemplates.com/find-templates

Still could end up costing a few bucks but figure at least less then half of what brand new badging would cost.