And the problem is that when the foreseeable future is over, it will be the 2030s and we'll probably have entirely new radical designs flying. Hydrogen propulsion, CFM Rise, blended wings, etc. etc. If Boeing are bleeding money and taking on expensive debt, how will they prepare for those times? If multiple of their designs are being years late, how will they have the engineering capacity to think of future designs?

Boeing the company is going nowhere. Boeing the commercial airplane maker is circling the drain in terms of how competitive they are. Their military and cargo jets, as long as the massive backlog, will keep them up for the next two decades easy. However if they can't improve themselves by next decade, they'll be forever behind.