well, I've only spent a couple minutes twinking, but I can tell you for sure that calculating and planning makes everything better. it's not a necessity, but I wouldn't be telling people NOT to calc, and just hope numbers magically appear; that seems a little bit backwards.
numbers don't change, calc'n the setup before you twink is pretty important if you want to know what you're capable of doing. starting a serious twink without a plan is generally a great way to end up with a half done twink project on hold until you get certain items you would have known you needed before hand had you planned it out.
maybe the idea is fine for beginning twinkers, since there's generally much more room for mistakes and improvements than on a max setup or extreme/unique twink.
most experienced twinkers will have their setup pinned within a few points before they even start. points don't appear out of nowhere. generally the only guesswork is access to contracts, or super rare items they may need to borrow.
if I misunderstood what you meant, sorry, but it seems like you're saying for them to just start equipping things without any idea what the end result will be or any planning on how to get it.
p/s/- nice initiative