After searching online and steam discussions about this problem that I never encountered when I first played this game years ago, I played 100+ hours with no real issue aside from that one stupid kobold that always manages to get past through my killbox somehow for whatever reason but jokes aside this no bootup thingy was something new for me and from the recent steam discussions I guess I am not alone with this problem. I click play and the game would just seemingly try to cycle over and over without any game screen loading in.

So I found this page from the devs themselves https://robotentertainment.zendesk.com/hc/en-us/articles/203163195-Orcs-Must-Die-2-doesn-t-look-like-its-launching-What-should-I-do
Basically it's simply telling you to do the normal stuff such as rebooting steam and then validating your files which I guess is pretty standard for anyone who has been using steam for quite some time now and I also did try to validate files initially when the game didn't launch, said there was 1 file corrupted/missing, downloaded it but it still didn't work. I then proceeded to also manually install DirectX via the files on the installer folder in your OMD2 folder, I did both the DXsetup and the vcredist_x86 and then I rebooted Steam. Once Steam launched again I once again validated my files again before trying to boot it up again, game didn't launch again once I tried it but this time Windows had a pop-up for me that one of the apps was needing something called DirectPlay right after I clicked Play on OMD2. I then let windows download and install this DirectPlay and then after all of that troubleshooting I finally saw the Title screen of OMD2 once again after about half a decade or so.

I am aware that this solution might not work for everybody since I am not really sure what the main problem is but at least someone who has the same problem can try doing the same steps as I did and see it that would work for them. I don't even know what DirectPlay is and why it only popped out now specifically for this game but I guess it's some kind of older thing given that this game is more than a decade old at this point. Anyways I hope I at least helped one person and could finally start blasting some orcs.

TLDR:
Manually install Direct X from installer folder
Reboot Steam
Validate Files
Try to launch the game
Windows popup about DirectPlay
Let Windows install DirectPlay
Hopefully OMD2 finally loads after this