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My goal originally was to strip the guitar down to the wood from a polyurethane finish and replace it with a nitrocellulose finish. However, I have had some issues removing the original finish via heat gun.

Do I remove the layer underneath the finish (I think it's a sealer coat) to get to the wood, or have I gone too far on the front?

If I have removed too much, what are possible solutions to even out the top?

I've even considered doing a wood carving in it if nothing else, so all ideas are considered.

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(Almost) any time you do a refinish you should go to bare wood and get all of the old stuff off. There is a good chance that whatever you put on top is not going to be completely compatible with the factory finish - particularly if its a catalyzed poly. Its also usually a real hassle to get the old stuff off. I've used chemical strippers followed by a fair amount of sanding.

Generally nitro wants to be on a compatible sealer - shellac, vinyl modified sealer or sometimes just some well thinned lacquer. I'm guessing your guitar is ash or alder so it shouldn't need any pore filling