1. To diversify their finances. Going all in means every bet, if it fails, could be your last. (Less applicable for someone with Elon's name recognition.)
2. Some ideas don't scale down. Building a big rocket is a different game from building a small one. The lessons from the latter will apply roughly, at best, to the former. Same with tunnels.
3. To get intellectual and political buy-in. When people invest in something, they take ownership--financially and emotionally. Having shareholders who you can deputies to fight your battles can sometimes beat a hired hand.
Loans are the simplest to understand -- it's leverage. If you think you can double your money in a few years with a business plan, and that opportunity scales passably well to more money than you have in your bank account, you can take out a loan. To use your language, leverage is just "betting on yourself" even harder.
Taking on investors is different in that you can't ruin yourself doing it, but similar in that it increases your resources in a way that you hope will more than pay off over time against the cost.
Musk probably doesn't feel like he needs that validation, so the main reasons to take outside money would be leverage and diversification. The downside is some loss of control.