Do the maps for the small buildings need to be on the same zoomy map as the overland long trips or can they be different maps loaded up with the same software ?

Are you after real time drawing of the lines and shapes or is this something you can draw non real time and add to the map ?

Are you after sharing the drawing lines, shapes and map updates with other people over the internet ?

Is it a requirement that someone can view the database using a web browser or could you use a specific app ?

I know of some apps that can do some or most of this but not everything on it. Were using leaflet here with our zoomable maps. Its possible that it can add lines and shapes and we use pins on ours. But I dont know of anything that will jump through time based mapping elements. Guild City is probably the best of ours to look at since it has several pins stuck into it.

https://www.cartographersguild.com/l...type=guildcity

But we dont have the ability to draw on top of it. However I know that the leaflet API has these things and I have seen some people use it.

I wouldnt say that leaflet would be the ideal choice either because its hard to change the background image to it. Leaflet is good for displaying maps that are finished. Your best option is to use a GIS package or a Virtual Table Top. There are several of those about but depends on how you answer the above questions would narrow it down.