Issues with Winbe and package dependencies?

Hi there, not really new to Trisquel or Linux per se but happy to make my first forum post after about 2 years of consistently using Trisquel!
Finally have encountered my first error that I am not really sure how to move forward with.

Currently I am trying to run an old 32bit program for Windows via Wine which under different distros I have had no problem doing so. In the past, all I had to do was enable i386 architecture and then install wine32:i386 and it was working without a hitch. However this is not working.

Running the program with wine from the terminal returns this

it looks like wine32 is missing, you should install it.
as root, please execute "apt-get install wine32:i386"
Application could not be started, or no application associated with the specified file.
ShellExecuteEx failed: File not found.

And this is where I would normally just install the missing packages and I an met with this mouthful

Solving dependencies... Error!
Some packages could not be installed. This may mean that you have
requested an impossible situation or if you are using the unstable
distribution that some required packages have not yet been created
or been moved out of Incoming.
The following information may help to resolve the situation:

Unsatisfied dependencies:
libapparmor1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libasound2t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libasyncns0:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libblkid1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libbrotli1:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libbsd0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libbz2-1.0:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libcap2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libcapi20-3t64:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libcom-err2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libcurl4t64:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libdb5.3t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libdbus-1-3:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libdeflate0:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libdrm2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libdw1t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libelf1t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libexif12:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libexpat1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libffi8:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libflac12t64:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libfontconfig1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libfreetype6:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libgcc-s1:i386 : Depends: libc6:i386 (>= 2.35) but it is not going to be installed
libgcrypt20:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgd3:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libglib2.0-0t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgmp10:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgnutls30t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgpg-error0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgphoto2-6t64:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libgphoto2-port12t64:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libgssapi-krb5-2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libgstreamer-plugins-base1.0-0:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
Recommends: gstreamer1.0-plugins-base:i386 but it is not installable
libgstreamer1.0-0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libheif1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
Depends: libheif-plugin-aomdec:i386 (= 1.17.6-1ubuntu4.8) but it is not installable or
libheif-plugin-dav1d:i386 (= 1.17.6-1ubuntu4.8) but it is not installable
Recommends: libheif-plugin-aomenc:i386 (= 1.17.6-1ubuntu4.8) but it is not installable
libhogweed6t64:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libicu74:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libidn2-0:i386 : Depends: libc6:i386 (>= 2.28) but it is not going to be installed
libjbig0:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libjpeg-turbo8:i386 : Depends: libc6:i386 (>= 2.7) but it is not going to be installed
libk5crypto3:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libkeyutils1:i386 : Depends: libc6:i386 (>= 2.7) but it is not going to be installed
libkrb5-3:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libkrb5support0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libldap2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libltdl7:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
liblz4-1:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
liblzma5:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libmd0:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libmount1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libmp3lame0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libmpg123-0t64:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libnettle8t64:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libnghttp2-14:i386 : Depends: libc6:i386 (>= 2.17) but it is not going to be installed
libogg0:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libopus0:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
liborc-0.4-0t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libp11-kit0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libpcap0.8t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libpcre2-8-0:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libpcsclite1:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libpng16-16t64:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libpsl5t64:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libpulse0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
librtmp1:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libsasl2-2:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
Recommends: libsasl2-modules:i386 (>= 2.1.28+dfsg1-5ubuntu3.1) but it is not installable
libsasl2-modules-db:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libselinux1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libsharpyuv0:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libsndfile1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libssh-4:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libssl3t64:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libstdc++6:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libsystemd0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libtasn1-6:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libtiff6:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libudev1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libunistring5:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libunwind8:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libusb-1.0-0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libvorbis0a:i386 : Depends: libc6:i386 (>= 2.29) but it is not going to be installed
libvorbisenc2:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libwayland-client0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libwebp7:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libwine:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
Recommends: libcups2t64:i386 (>= 1.4.0) but it is not installable
Recommends: libgl1:i386 but it is not installable
Recommends: libodbc2:i386 (>= 2.3.1) but it is not installable
Recommends: libosmesa6:i386 (>= 10.2~) but it is not installable
Recommends: libsdl2-2.0-0:i386 (>= 2.0.12) but it is not installable
Recommends: libv4l-0t64:i386 (>= 0.5.0) but it is not installable
Recommends: libvulkan1:i386 (>= 1.2.189.0) but it is not installable
Recommends: libxcomposite1:i386 (>= 1:0.4.5) but it is not installable
Recommends: libxcursor1:i386 (> 1.1.2) but it is not installable
Recommends: libxfixes3:i386 but it is not installable
Recommends: libxi6:i386 but it is not installable
Recommends: libxinerama1:i386 (>= 2:1.1.4) but it is not installable
Recommends: libxrandr2:i386 but it is not installable
Recommends: libxrender1:i386 but it is not installable
Recommends: libxxf86vm1:i386 but it is not installable
Recommends: libgl1-mesa-dri:i386 but it is not installable
Recommends: libasound2-plugins:i386 but it is not installable
Recommends: gstreamer1.0-plugins-good:i386 but it is not installable
libx11-6:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libxau6:i386 : Depends: libc6:i386 (>= 2.33) but it is not going to be installed
libxcb1:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libxdmcp6:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libxext6:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
libxkbcommon0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libxkbregistry0:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libxml2:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
libxpm4:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
libzstd1:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
ocl-icd-libopencl1:i386 : Depends: libc6:i386 (>= 2.34) but it is not going to be installed
wine32:i386 : Depends: libc6:i386 (>= 2.38) but it is not going to be installed
zlib1g:i386 : Depends: libc6:i386 (>= 2.4) but it is not going to be installed
Error: Unable to correct problems, you have held broken packages.
Error: The following information from --solver 3.0 may provide additional context:
Unable to satisfy dependencies. Reached two conflicting decisions:
1. libc6:amd64 is selected for install because:
1. dpkg:amd64 is selected for install
2. dpkg:amd64 PreDepends libc6 (>= 2.38)
2. libc6:amd64 is available in versions 2.39-0ubuntu8.8trisquel1, 2.39-0ubuntu8.3trisquel1
but none of the choices are installable:
- libc6:amd64=2.39-0ubuntu8.8trisquel1 is not selected for install because:
1. wine32:i386=9.0~repack-4build3 is selected for install
2. wine32:i386 Depends libc6:i386 (>= 2.38)
3. libc6:i386 is available in versions 2.39-0ubuntu8.7trisquel1, 2.39-0ubuntu8.5
[selected libc6:i386=2.39-0ubuntu8.7trisquel1 for install]
4. libc6:i386=2.39-0ubuntu8.7trisquel1 Breaks libc6 (!= 2.39-0ubuntu8.7trisquel1)
[selected libc6:i386=2.39-0ubuntu8.7trisquel1]
For context, additional choices that could not be installed:
* In libc6:i386 is available in versions 2.39-0ubuntu8.7trisquel1, 2.39-0ubuntu8.5:
- libc6:i386=2.39-0ubuntu8.5 is not selected for install
- libc6:amd64=2.39-0ubuntu8.3trisquel1 is not selected for install

The last bit where it says it is in certain Trisquel repos but is uninstallable is what is throwing me as this is the first time I have run into something like this. I only have two "contrib" packages installed which are tor-browser-launcher downloaded from Debian directly as a .deb and then Oracle VirtualBox as the software itself is GPL3 and only the add ons are proprietary. Just to be safe, I removed both of those via apt, ran autoremove, and updated apt just to see if it would self correct. It did not.

I am not really new to Linux but this is my first personal encounter with what I think is referred to as "dependency hell". Any help would be greatly appreciated