S.G.
Keep in mind he will be three soon, and that most kids tend to grow up a lot between two and three years. When my boys were three there would be no way they would sit in a stroller, they had long since given up napping and they were also past the stage of running off. I would suggest just using the umbrella stroller, or try to find a better stroller second hand. As three year olds they were helping to push the luggage cart.