I don't know if he'll find anyone gullible enough to buy it. At least not until after bankruptcy. Who would buy that company that doesn't make a profit and has that much debt? Only an idiot like Musk would do that.
At a significant discount it can be appealing just for the amount of user data and reach. Someone bought yahoo then sold it to another one. Not good example of success but example of looking at the price and saying what the heck I'll take the risk.
Even with a significant discount you would be taking on $1b just in interest a year for a company that doesn't make money. You somehow have to make $1b just to break even.
If I could buy Twitter I bet I could do a better job than its current owner. Best I can do is a quarter and some pocket lint, and I'm really taking a gamble here.