In previous episodes, Walter states that Robert Queen is one of his oldest friends. In this episode, he refers to Moira as "Mrs. Queen" and seems to have a purely professional relationship with Robert, both just days prior to the Queen's Gambit leaving on its ill-fated voyage.
(at around 28 mins) During a flashback, the pizza box that Oliver puts on the bed is closed/open/closed before Oliver actually opens the box. And it appears that half the pizza is missing.
The song "bleeding love" plays in the flashback scene. However, the song wasn't released in the US until after Oliver was on the island.
An insurance company is not going to push to pay out. An insurance company would do the exact opposite and use any reason they can to not pay.