Since I felt like being mean to myself I went with a pretty bone heavy design. As some of you may have noticed parenting to bones is pretty easy to mess up and I struggled quite a while with objects completely changing location when parenting these objects to bones, but after some experimentation I managed to find a way to avoid such issues.
1: Select your object and parent it directly to the desired bone (Not the armature) This should at this stage not show any visible effects.
2: Select the object again and parent it to the armature. This should result in the previously parented bone becoming the main parent, as seen in the relations section under Bone data.
If this little tip worked for anyone else then please confirm it in this thread. Me alone is a pretty small sample size so I’m pretty much hoping that these steps wasn’t a fluke on my part.