Yeah, I usually don't try for too long trying to get that "perfect" item, otherwise it starts to feel like a boring excercise. And it's usually not necessary, maybe unless you're looking for a specific thing to take with you to the end. My last time through I ended up with like 19 various charm quality 4-5 items stuffed in barrels outside the shop, so it turns out that collecting and hoarding them was pretty much a waste.
BUT for a few items, yeah I'll reload a few times. I reloaded one particular piece of armor in Aleroth until it was a charm 5 (luckily it only took three tries)...and I'm still wearing it at lvl 30, and don't intend on giving it up anytime soon either