Wow, that sounds like a lot of work! That's really cool, Fin! Responding to your points.
1. That seems reasonable to start. We can try to finalize what we wish to change/include, and if we wanted, somebody could re-create the maps for a final version.
2. I'd have to see how it looked to decide if a printed font works. I think changing it on the map directly is the best idea. They cost money, but the fonts from
https://www.mytolkienbooks.com/tolkien-fonts/ would probably work best.
3. Map V is indeed pretty rough.
- Not sure I entirely understand your question about the Anduin, I may need to look at the map itself to understand it.
- Adding in Tol Eressëa and the shadowy Isle by combining Maps IV and V makes sense.
- I agree that adding things (like forests or other rivers) by guessing isn't in the spirit of the project, I would simply clean up what Tolkien himself drew.
- I agree with removing the attempt at the coast line from the mouth of the Sirion to the mouth of the crossed out branch of the Gelion.
- I agree with you assessment that this line appears to be the Narog, along with tributaries to Lake Mithrim. I say we let it stand.
- I think attempting to add the Yellow Mountains would involve too much guess work. It is reasonable to assume they were destroyed during the War of Powers.
- I agree with all of your textual/legend changes. I'm OK with simply removing the labels showing the cardinal directions (north, north-west and the two souths), they do not add much to the map and are situated in confusing locations.