Would definitely be interested in your Quests (any runs you "finish" D21 or earlier! [ie "end" bank quest] )
Pretty rare can even do all easy quests w/o upgrades! (buy/luck only) Eg, "Obsidian Axe" (needs 10 Obs just to MAKE!
I have same problem---takes good luck 2 find useful tools in short time---but DIFFERENCE is *HUGE*! (even "none" vs "Steel")
if you only get stone, not much benefit. Fishing rod's don't help as much (~20% cloth) UNLESS u get the hi end stuff (EXPENSIVE! to buy!)
But hi quality knives help w meat & leather; + (new version) Tailor.
I just know if I'm gonna *GRIND* it all the way out to D29+ (UGH) Best to MAX tools & upgrades. (steel min; Mythril is better)
Will have to try a run w a Zeph to the capital. (very hard to get unless they're you're 1st two)
Chests----do you know if Wits impacts chest "luck"? (often mine fail/jam, even w thief)
Best is thief + Engineer, but takes *LOTS* of Guild points!