You don't have to be rich to afford a 4.4 Android device. I have a contractless 4.4 piece of shit "top 4 brand" on my country's best network for $30. however, i fully expect there to be no updates. ever.
there are a small handful of ways to get a phone that'll be updated once in a while for under $100-200, you just have to nerdily search exhaustively.