I think the problem with the program crashing AutoCAD 2025 was, I was calling the CheckDrawing number routine directly after loading it with ACADDOC.lsp file. I moved the call to the DocumentManager.DocumentCreated event which fires when the drawing opens and AutoCAD stopped crashing on Insertion of Objects.
I found this if I hit ctrl+alt+P. Was hoping it would help with the above Managed coreCLR error.

I hit select and added Managed .net Core and Native code. And the debugger still gives the same error.
This is my .vbproj file. Contents
<Project Sdk="Microsoft.NET.Sdk">
<PropertyGroup>
<TargetFramework>net8.0-windows</TargetFramework>
<Nullable>enable</Nullable>
<OutputType>Library</OutputType>
<RootNamespace>Check_Drawing_Number</RootNamespace>
<MyType>WindowsFormsWithCustomSubMain</MyType>
<IsWebBootstrapper>false</IsWebBootstrapper>
<PublishUrl>publish\</PublishUrl>
<Install>true</Install>
<InstallFrom>Disk</InstallFrom>
<UpdateEnabled>false</UpdateEnabled>
<UpdateMode>Foreground</UpdateMode>
<UpdateInterval>7</UpdateInterval>
<UpdateIntervalUnits>Days</UpdateIntervalUnits>
<UpdatePeriodically>false</UpdatePeriodically>
<UpdateRequired>false</UpdateRequired>
<MapFileExtensions>true</MapFileExtensions>
<ApplicationRevision>0</ApplicationRevision>
<ApplicationVersion>1.0.0.%2a</ApplicationVersion>
<UseApplicationTrust>false</UseApplicationTrust>
<BootstrapperEnabled>true</BootstrapperEnabled>
<GenerateAssemblyInfo>false</GenerateAssemblyInfo>
<UseWindowsForms>true</UseWindowsForms>
<ImportWindowsDesktopTargets>true</ImportWindowsDesktopTargets>
<Copyright>Copyright © </Copyright>
<AssemblyVersion>1.0.0.0</AssemblyVersion>
<FileVersion>1.0.0.0</FileVersion>
<StartupObject>Check_Drawing_Number.</StartupObject>
</PropertyGroup>
<ItemGroup>
<FrameworkReference Include="Microsoft.WindowsDesktop.App" />
</ItemGroup>
<PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Debug|AnyCPU' ">
<DocumentationFile>Check-Drawing-Number.xml</DocumentationFile>
<NoWarn>42016,41999,42017,42018,42019,42032,42036,42020,42021,42022,42353,42354,42355</NoWarn>
</PropertyGroup>
<PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Release|AnyCPU' ">
<DefineDebug>false</DefineDebug>
<DocumentationFile>Check-Drawing-Number.xml</DocumentationFile>
<NoWarn>42016,41999,42017,42018,42019,42032,42036,42020,42021,42022,42353,42354,42355</NoWarn>
</PropertyGroup>
<ItemGroup>
<Reference Include="AcCoreMgd, Version=19.0.0.0, Culture=neutral, processorArchitecture=MSIL">
<SpecificVersion>False</SpecificVersion>
<HintPath>C:\ObjectARX 2025\inc\AcCoreMgd.dll</HintPath>
<Private>False</Private>
</Reference>
<Reference Include="AcDbMgd">
<HintPath>C:\ObjectARX 2025\inc\AcDbMgd.dll</HintPath>
<Private>False</Private>
</Reference>
<Reference Include="AcMgd">
<HintPath>C:\ObjectARX 2025\inc\AcMgd.dll</HintPath>
<Private>False</Private>
</Reference>
</ItemGroup>
<ItemGroup>
<Compile Update="ConfigForm.Designer.vb">
<DependentUpon>ConfigForm.vb</DependentUpon>
</Compile>
<Compile Update="My Project\Application.Designer.vb">
<AutoGen>True</AutoGen>
<DependentUpon>Application.myapp</DependentUpon>
<DesignTime>True</DesignTime>
</Compile>
<Compile Update="My Project\Resources.Designer.vb">
<AutoGen>True</AutoGen>
<DesignTime>True</DesignTime>
<DependentUpon>Resources.resx</DependentUpon>
</Compile>
<Compile Update="My Project\Settings.Designer.vb">
<AutoGen>True</AutoGen>
<DependentUpon>Settings.settings</DependentUpon>
<DesignTimeSharedInput>True</DesignTimeSharedInput>
</Compile>
<Compile Update="OnDrawingCheck.Designer.vb">
<DependentUpon>OnDrawingCheck.vb</DependentUpon>
</Compile>
</ItemGroup>
<ItemGroup>
<None Update="My Project\Application.myapp">
<Generator>MyApplicationCodeGenerator</Generator>
<LastGenOutput>Application.Designer.vb</LastGenOutput>
</None>
<None Update="My Project\Settings.settings">
<Generator>SettingsSingleFileGenerator</Generator>
</None>
</ItemGroup>
<ItemGroup>
<BootstrapperPackage Include="Microsoft.Net.Client.3.5">
<Visible>False</Visible>
<ProductName>.NET Framework 3.5 SP1 Client Profile</ProductName>
<Install>false</Install>
</BootstrapperPackage>
<BootstrapperPackage Include="Microsoft.Net.Framework.2.0">
<Visible>False</Visible>
<ProductName>.NET Framework 2.0 %28x86%29</ProductName>
<Install>false</Install>
</BootstrapperPackage>
<BootstrapperPackage Include="Microsoft.Net.Framework.3.0">
<Visible>False</Visible>
<ProductName>.NET Framework 3.0 %28x86%29</ProductName>
<Install>false</Install>
</BootstrapperPackage>
<BootstrapperPackage Include="Microsoft.Net.Framework.3.5">
<Visible>False</Visible>
<ProductName>.NET Framework 3.5</ProductName>
<Install>false</Install>
</BootstrapperPackage>
<BootstrapperPackage Include="Microsoft.Net.Framework.3.5.SP1">
<Visible>False</Visible>
<ProductName>.NET Framework 3.5 SP1</ProductName>
<Install>true</Install>
</BootstrapperPackage>
<BootstrapperPackage Include="Microsoft.Windows.Installer.3.1">
<Visible>False</Visible>
<ProductName>Windows Installer 3.1</ProductName>
<Install>true</Install>
</BootstrapperPackage>
</ItemGroup>
</Project>
Any help would be much appreciated.