Great. Means your issue is caused by the bug I stumbled over. Turns out notes also live on a sheet, so if you accidentally delete the one they're on (which there is no way to tell) you also delete the notes. Seems like they're on the LAND sheet for lot of the official templates (by pure coincidence), but no guarantee all templates are like that (probably not, since city and dungeon styles don't have a LAND sheet at all).

I've reported this to the appropriate authorities.

No, not that easily. If you are willing to do it with an effect, you can very easily draw a polygon along the road and use the color key effect to knock out those parts, otherwise you'll need to either redraw or modify the polygons.

Keep in mind that the drawing tools have a trace feature, so it is quite easy to draw a new poly that follows along part of the old one, and then draw the part along the road manually.

You ask about text, but you also talk about things like political borders and stuff, so it seems like that should be taken into consideration.

Now, to start, I personally hate PhotoShop, I find it cumbersome, difficult and intuitive to use, and on top of that, expensive. But, there are other image editors out there so I'll not jump to the conclusion of using CC3+ just because I don't like the other option.

But, you obviously isn't skilled in PS yourself, given that you don't know the difficulty of working with text, which more or less brings me to a conclusion right away, use what you know. If you know how to do things in CC3+ there isn't really a good reason to use an image editor, unless you want to use it more as a training exercise to learn that software rather than use what would be most appropriate for you.

Considering that both options do allow a layered approach, both can be used for the task, but if you import the map to scale in CC3+ before drawing on top of it, you can also use various tools to do things like measuring length and area, including measuring length along a curved line, which I personally find extremely nice when working with maps, so I would probably pick CC3+ for that option alone.

The only reason where I feel the image editor may be a bit stronger is making the things you draw on top of the scanned image appear better "integrated" into the image. But this is something that takes skill with the image editor, it doesn't come for free, and you can get a long way in the same direction by using sheet effects.

Few more maps today, this time it is my entry.

You can insert an image into your map using Draw -> Insert file. You can then either place this on a sheet below the one you draw on, or add a transparency effect to the sheet holding the image if you wish to have it as an overlay.

CC3+ has a command called TRACED than can construct an entity from an image automatically, but this works best if the image is black landmasses/transparent seas, and it will only be able to handle the outline, it can't really do inland contours and things like that (unless you are able to extract those manually as a separate image to be processed.)

Yes. There are a couple of ways to go about that. All the options do require some manual work to get a good end result, but getting the coastlines is quite simple (Although you do probably want to add additional detail to a zoomed in part of the world). See here for one way to do it