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1. How broke is Green Arrow?
-Hes dressed rather smart for someone whos broke.
-He could afford a hospital room for Speedy.
-Hes able to afford to run several vaults fully equipped with weaponry and the electrical bill that comes with it. He also repaired the damage from the bomb Speedy planted in it.
-He can afford arrows for himself and his protege.
-He can support himself and Roy (and probably also the medical bills that come with sending him to therapy, etc.)
2. How successful is Bowhunter Security?
3. How was Roy a shareholder in Bowhunter despite being a minor? Was Ollie a caretaker for his share as his guardian?
4. Did Ollie help Will start his Private Security business? How did he find investors for it?
1. He's not destitute. He's just not a millionaire any longer. You're assuming he paid for Speedy's healthcare, but that's not a safe assumption. The League has funds for that sort of thing. Also, Oliver set up a substantial trust for Roy before Oliver lost his fortune. That trust went to Will, but he's since given the bulk of that over to Roy.
3. Roy's no longer a minor. Technically, i.e. legally and chronologically, he's about 28 during Season Four.
4. No. (I mean he didn't hinder it, but he didn't help financially in any way either.)
4a. By "he" do you mean Will or Ollie?