Lots of inaccuracies in your recalling of his biography.

He also sold his first company near the height of the dotcom bubble for an obscene amount of money.

The company was Paypal, and it was sold after the bubble had burst. It was sold for $1.5 billion, of which Musk's take was 10-15%. Musk however was against the sale, he seems to have more of a buy and hold outlook. And he was right, Paypal is about to be spun out of eBay and will have a market cap of $50 billion. It certainly was not the case of someone getting lucky by selling a lemon at the height of the bubble.

SpaceX's early NASA contracts was essentially undeserved (it was something like right after three failed launches in a row).

Rockets do fail. You fix what made the rocket fail the first time and launch it again. There are military rockets that have had the same development trajectory, where you have 2 or 3 failures right at the start of the program. I haven't heard anyone make the case that NASA contracts awarded to SpaceX were "unfair." Even the biggest SpaceX detractors, of which there are plenty, don't try to make that point.

I've heard it argued that Tesla would have gone under without a government bailout

There was no bailout for Tesla. Tesla did get government loans in order to build out production capacity for the Model S. This loan program was ran by the Department of Energy and existed before the financial crisis began. In order to qualify a company had to demonstrate that they had an electric vehicle whose production was ready to be scaled up. It was supposed to be the same sort of thing the DOE does for nuclear power plants.

Overall I'd say Musk is extremely good at broad strategy. I could get into a lot more granular detail explaining the strategies that Musk outlined to make SpaceX and Tesla a success where so many others had tried and failed. Those strategies came from Musk himself. It was not the case of someone hiring others to come up with good ideas and implementing them yourself. And he does understand the technical guts of what he's working with.

I can't really wrap my head around how you could attribute his whole career to extreme luck. I guess it's the Elon Musk anti-circle jerk that is a natural reaction to the regular Elon Musk circle jerk. But things don't just happen on their own, people have to make them happen themselves. I do think it's entertaining the number of people on reddit that take the position that someone else's accomplishments were easy or obvious. If that's the case you would go do it yourself, but then you would see just how hard these things are.