So, quick update:
Managed to resize and clone, but wasn't able to boot from the cloned drive. Retried with Macrium, same problem. After much research I've managed to fix it. Seems there was an issue with the Master Boot Record (MBR) on the clone-drive.
For anyone with the same issue trying to follow along *proceed at your own risk, the following is prone to error, involves making edits in system32 through command prompt and may ruin your drive further*.
What I ended up doing to solve the issue:
Created installation media USB drive
Installed cloned drive into laptop (doesn't boot, but contains OS)
Booted from USB drive with windows installation media to access command prompt thru troubleshoot function
Tried following this guide to repair the master boot record (using the bootrec commands listed):
Cloned Drive Won't Boot | How to Make Cloned Drive Bootable?
When running into an access denied prompt with the bootrec /fixboot command, wound up on this guide:
https://www.partitionwizard.com/clone-disk/bootrec-fixboot-access-is-denied.html?amp
Following the above guide, ran into a hitch on step 12, for which I used this video:
and poof, i was in Windows!
Imagine reinstalling Windows like a pleb, ha!