I took the advice of ​ and decide to take a stab at using hole series. If you are not familiar with this tool it is a decent start to fastener workflow but it has plenty of room for improvement. Here's my biggest issues:

1. When locating holes the user feedback says: "Sketch the location for all new holes or slots..." and then you get the ribbon bar with some limited sketching tools. That's great because I want my holes located in rectangular pattern. So I attempt to select the rectangle by center sketch tool...only I can't get SW to change the sketch plane orientation. That means I can't create my construction geometry on the plane I need.

1B. And fix the blasted undo function inside the sketcher- it's the worst I've had to suffer through!

2. Ability to rename the hole series and have name propagate to child components.

3. Do not allow the ability to delete a middle hole while editing the piece part. I would prefer that the feature have some sort of lock mechanism to stop this from occurring. This is a feature level assy and should only be treated as such. If you do delete a middle hole I have had mixed results where some holes are deleted and when you edit the assy feature it says that "Some components containing hole series holes are suppressed and will not be edited." This is not the case. No components are suppressed neither are the missing hole features suppressed- they are deleted. I have yet to figure out how to reselect the middle components to get the feature to update. I have also had the next level component holes disappear as well.

4. Anytime you edit the hole series the end component selection appears blank and appears that it has to be redefined.

5. Ability to use own fasteners and not toolbox "components".

I've only started to explore this tool but this is my list of issues so far. I'm hoping I'm missing some check box or options somewhere.