I think I'd rather be launched into the sun over Jupiter. The sun you die pretty quickly as you get closer to it. I can't imagine there's much that could stop heat once you get past Mercury. Jupiter though? Jupiter is fucking spooky. Its core is hot like any molten core, but there's no crust. You'd fall through the sky and just keep falling for hundreds of miles. You'd eventually die from the heat like you would with the sun, but you wouldn't be able to see anything. At some point all you can see is goop. It's like being underwater in the Mariana Trench, but the water is nitrogen, metallic hydrogen, and liquid silicone.

Just launch lots of tiny bits of processed earth at them super fast. More propellant efficient and you don't have to worry that they might have packed a parachute.

You'd still be moving some 30km/s around the sun, and need to decelerate from that speed.

New slogan: Launch all billionaires straight up into the air using one of those circus cannons

If we're going for a bigger target, let's go all out and aim for Stephenson 2-18. Go big or go home!

That's an interesting question. A regular sail can sail into the wind, but they have a triangular sail, and a keel with water resistance. I don't think any of those things exist in space, so I'm going to guess no. Perhaps some sort of high efficiency propellant keel could make it possible?