That’d be super helpful! I’m doing something similar at the moment as well
OpenStreetMap community
Everything #OpenStreetMap related is welcome: software releases, showing of your work, questions about how to tag something, as long as it has to do with OpenStreetMap or OpenStreetMap-related software.
OpenStreetMap is a map of the world, created by people like you and free to use under an open license.
Join OpenStreetMap and start mapping: https://www.openstreetmap.org.
There are many communication channels about OSM, many organized around a certain country or region. Discover them on https://openstreetmap.community
https://mapcomplete.org is an easy-to-use website to view, edit and add points (such as shops, restaurants and others)
https://learnosm.org/en/ has a lot of information for beginners too.
You could manually draw polygons in a umap to do this. Or you could use an Overpass Turbo query to show all the ways you edited recently to have a visual of where you have and haven't worked. I can give you some queries to start with if you like.
Unfortunately, I don't know what any of those are. Sound complicated.
OpenStreetMap offers so many new things to learn :) Here's an example overpass query for myself: https://overpass-turbo.eu/s/1FG7 Just move the map to you area of interest, and in the code change the "user" to your username. Then click "Run" (or something similar, depending on the language). You can change the "way" part to "node" or "nwr" to extract different types of data. Or you can add ["building"] to just show buildings you last touched. Minor warning is that this shows things you were the last to edit. So if someone else is active in your area, your edits will disappear. If you've been active for a while, but only see your recent changes, we can add (newer:"2023-01-01T00:00:00Z") near the username.
http://umap.openstreetmap.fr is really pretty self-explanatory. It is similar to Google MyMaps, but built by the OSM community. A beginner's guide is available here: https://wiki.openstreetmap.org/wiki/UMap/Guide
I once had to place a bunch of different stuff on a video game map. To keep track of where I'd been, I loaded a picture of the game map into Photoshop and made a new layer (partially transparent) so I could color in areas once I was finished with them.
Photoshop itself is obviously massively overkill for this, but it did work pretty well. Transparency and either the brush or lasso-and-fill is all you really need.
Yeah, GIMP was my backup plan. It would just be hard to read the street names.