This makes very little to no sense to me. It'd make much more sense to invest in local talent, and get percentages from their success -- rather than just become a jack of all trades.
For Weed, time itself is money. Any living breathing moment he does not spend on completing quests and selling items, he is losing money. The turnover from his time invested in learning these basic, beginner skills -- and the time he can put in hunting or creating sculptures (which can surely sell to NPCs for a shit ton of money) -- is laughable. And the very idea that a crowd will form around him, and be taken aback by his beginner-level proficiency, is absurd.
Nothing about this makes sense.