Is it possible to compile VS project in debug version including breakpoints to be debugged via a different project?

hop of those help? Rekaszeru's answer to this question shows how to set up Eclipse in order to always launch the previously launched application.
You simply have to go to preferences / run-debug / launching and check the "Always launch previously launched application" box as he shown in the picture he used to illustrate his answer:

wish of those help I assume you do not need assistance with creating the MSBuild task to satisfy your first criteria.
To delete files and zip, try something like this:

<Import Project="$(MSBuildExtensionsPath)\MSBuildCommunityTasks\MSBuild.Community.Tasks.Targets"/>
<Target Name="SomeTarget">

<ItemGroup>
    <FilesToDelete Include="Path\To\Debug\*.pdb"/>
    <DebugApplicationFiles Include="Path\To\Debug\*.*"/>
</ItemGroup>

<Delete Files="@(FilesToDelete)" />

<Zip Files="@(DebugApplicationFiles)"
  WorkingDirectory="Path\To\Debug"
  ZipFileName="Where\To\Store\Zip\Foo.zip"
  ZipLevel="9" />
</Target>

this will help You might be able to put a Debugger.Launch() statement in place of a breakpoint. I have had to use this many times when debugging applications that I don't control the application start and need more of a remote debugging scenario. The Debugger.Launch() will allow you to attach a new or existing VS instance to a running application.
By doing that in your scenario, you can start to inspect the threads (both in your current VS, and any new VS you attach with the Debugger.Launch() to ensure that they are both aware of the same threads. Your original VS may be losing access to the threads that your callback are on and thereby is unable to break.

To fix this issue When working with multiple maven projects, I find it convenient to put both under a parent maven project. The two child projects are not aware of the parent and remain independent of each other, but by aggregating them on one parent pom, you can conveniently build and test them at the same time, keeping the dependent in sync with its dependency. When you do that, you can also create Run configurations for each project, launch them in debug mode, and put breakpoints in either or both of them.
The parent pom stays in the parent folder of both projects, and does not need to go into source control because the child poms don't refer to it as their parent--its only for your convenience in working on both at the same time. Such a pom might look like:

<?xml version="1.0" encoding="UTF-8"?>
<project xmlns="http://maven.apache.org/POM/4.0.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/maven-v4_0_0.xsd">
    <modelVersion>4.0.0</modelVersion>

    <groupId>anything</groupId>
    <artifactId>anything</artifactId>
    <version>0.0-SNAPSHOT</version>
    <packaging>pom</packaging>
    <name>All projects</name>
    <modules>
        <module>project-1-subdirectory</module>
        <module>project-2-subdirectory</module>
    </modules>
</project>

I hope this helps you . Go to the Project properties → Security, and then uncheck "Enable ClickOnce Security Settings". Now it debugs and runs again without the error.