Keeping this as basic as possible but hopefully elaborate enough to get the status of the current ability / limitation in this regard.
I have 2 Macs that run everything out of iCloud (Essentially iCloud is the unified storage of my system, while accessing said data via a Laptop and Desktop).
Are there any software constraints or considerations worth noting that would prohibit me from, or somehow impair the hypothetical option of running the same &/ separate macros in two separate applications, one being on each individual machine?
I do have Macros Syncing successfully Apple Handoff is disabled to prevent mixed system clipboard data
Sorry for the "basic" question but I didn't find anything explicitly pertaining to this and would love to know what power I hold
You shouldn't have any problems running the same Macros on two different machines simultaneously.
Keyboard Maestro stores the values of Global Variables, Local Variables and Dictionaries locally (i.e. not in iCloud) so, they are unique to each machine.
The only possible (and highly unlikely) problems I can think of would be:
Two people editing (i.e. not running, but making changes to) exactly the same Macro at exactly the same time in the Keyboard Maestro Editor.
If two people were running a Macro at the same time that wrote data to the same shared file in iCloud.
I have indeed noticed occasionally some files (It was in fact the "Keyboard Maestro Macro.plist" that got caught ) storing it either here or there in the local device Lib > Application Support area
Thank you very much for your insight as well! I am going to do a little further interest based exploration of the mentioned "Global Variables, Local Variables and Dictionaries" values. Also semi-off topic but hopefully not too much... I am trying to decide (mostly specifically for KM now) wether I should be learning how to execute AppleScripts, JavaScript, XML, or Shell, FIRST to be most effective in setting Macros up for myself. Do you, or anyone else reading have any input that I could take to heart on that?
The advice that seems to be given most often on the Forum about how to learn to use Keyboard Maestro, is to learn by building Macros to solve real problems rather than just learning for the sake of learning. Of course there's no harm looking into AppleScript if you find it interesting - but it's not necessary.
When you get stuck, do a Google Search with "Keyboard Maestro" in the search. There is lots of info in the Keyboard Maestro Wiki and Manual and plenty of past topics and solutions in the threads on this Forum.
And Macros don't have to be complicated to be useful.
Just having a Macro that uses a hotkey to open a Folder that you find yourself needing to open several times a day can save hours of time.
Here is a good article, an interview with Keyboard Maestro's developer @peternlewis where he gives some good advice on how to learn to use Keyboard Maestro (I could have avoided typing everything above if I had just pasted this link... )
It really depends on what you are doing in your macros. AppleScript is good for manipulating or getting information from applications if they support it, and it's UI scripting can sometimes take you places KM can't reach. JavaScript for Automation helps similarly, plus there's a lot more "real programming" built in (Arrays! Dictionaries!) and JavaScript itself is great for direct interaction with web forms and so on. Shell scripting opens up the wealth of Unix utilities already on your Mac -- sed and awk for text processing, curl for URLs, etc.
Each has it's advantages and failings, there's a lot of crossover -- and you can get along fine in KM without knowing much about any of them! If you do as @Zabobon suggests above and try making things useful for yourself, then search/ask here if you get stuck, you'll pick up any "external" scripting you need as you go along.
) storing it either here or there in the local device Lib > Application Support area 
)