Basically, I'm making a lot of progress drawing in buildings and upgrading sidewalks to modern standards in my city, but sometimes I lose track of what I have and haven't done yet. As simple as highlighting the areas I've finished in a colour, is there a way I could track this? I'm willing to use any kind of tool for the job.
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.
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.
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.