No, not getting hit is king. I am on NG+++ and have encountered absolutely zero chokes really (and PVP invasions generally end up in my favor to say the least). Learning to play the game properly with "lesser gear" (which is a weird term for Souls game equipment where they atleast attempt to balance things via different stat scalings and etc) the first time through means that you will never encounter problems, ever. I can practically speed run the game now.
Basically anything that subverts challenge in Dark Souls via wasting a lot my time I have no real interest in doing in the Souls games (especially when you could just... keep playing the game and get those materials naturally while also progressing at the same time - in a faster time span).
Gear transfers to NG+ and beyond. If you have upgraded it in NG then you never have to worry about it again. I'm not sure how upgraded gear subverts challenge, especially coming from a guy who has probably upgraded Vitality and other stats. If you aren't doing an SL1 naked calamity ring non-backstab punching run, you're messing with the true challenge of never getting hit and playing the game "properly."
It would take you several playthroughs to amass the amount of titanite slabs through natural drops needed to fully upgrade sets of armor and weaponry. It's beneficial to get everything out of the way in NG where you have all the embers and where it's quickest - upgrading things, picking up every item, etc - so that subsequent playthroughs are purely focused on progression and experimentation.