VS2019 V16.6.3
For me the problem was somehow the main .proj file ended up with an entry like this for the project whose DLL wasn't getting copied to the parent project bin folder:
<ProjectReference Include="Project B.csproj">
<Project>{blah blah}</Project>
<Name>Project B</Name>
<Private>True</Private>
</ProjectReference>
I manually deleted the line <Private>True</Private>
and the DLL was then copied to the main project bin folder on every build of the main project.
If you go to the reference of the problem project in the references folder of the main project, click it and view properties there is a "Copy Local" setting. The private tag equates to this setting, but for me for some reason changing copy local had no effect on the private tag in the .proj file.
Annoyingly I didn't change the copy local value for the reference, no idea how it got set that way and another day wasted tracking down a stupid problem with VS.
Thanks to all the other answers that helped zone me in on the cause.
HTH