The Wager reminds me a bit of Strange Adventures in Infinite Space, Digital Eel's excellent game of space exploration. In The Wager, however, you are exploring an archipelago in a sailing ship, rather than a stellar arm in a starship. The basic dynamic is similar, however; you encounter things that earn you money, and must earn enough by the end of the game or you lose. In Strange Adventures, this is because you are in debt; in The Wager, there's supposedly another adventurer doing the same as you, and you must discover more valuable stuff than he. (This is entirely notional, however, since you never encounter an island and are told that someone else got there first.)
It has a pleasingly retro look, like a DOS game from the late 80s in EGA graphics, and the occasional little narrative bits are entertaining. Indeed, I could easily see this game being a commercial hit in 1988 or so. Mild fun, but not bad, particularly for a game originally done in 72 hours for a Ludum Dare (though expanded a bit afterward).