@Tippon Imagery often needs to be re-aligned to match up with local traces. The wiki has some guidance on the general "Using Aerial imagery" pages and on handling off axis imagery on the page for roof modelling.
https://wiki.openstreetmap.org/wiki/Using_aerial_imagery
https://wiki.openstreetmap.org/wiki/Roof_modelling
@sic_semper_tyrannis
If you can get the parcels from the municipality then you can probably give them a false OSM tag that renders and convert to show on OsmAnd via OsmAndMapCreator (then sideload them). It might be best to convert the addresses to OSM format too so they display.
Alternately there are two apps for putting QGIS projects on a mobile phone: QField and Merging/Input. They are meant for data collection but can be used to just display things as well.
I think we're missing a tonne of Lucy's "thought process" from the "we have to move on" that seems to happen after her prizes.
If you're adding from an external source make sure you've checked the licence is OK, not everything that's "open data" is as permissive as OSM requires.
https://wiki.openstreetmap.org/wiki/Import/ODbL_Compatibility
@Tvkan
Not PNG/JPEG, but as you mention Inkscape then maybe a SVG extract would work for you?
This site does several SVG styles:
https://extract.bbbike.org/
If you would prefer this offline there's a "community style" for OsmAnd that goes for a very similar look here:
https://github.com/OsmAnd-Rendering/Cycling/blob/main/README_EN.md
I think Trail Router is the simplest OSM based "give me a route" tool.
@governorkeagan
I've never used it, but there's a location sharing plugin for OsmAnd that shares location via Telegram:
https://osmand.net/docs/user/plugins/osmand-tracker/