Apple was "near bankruptcy" in the post-Jobs 90s period of the late 90s. Closer to the time of the 1997 CRT iMac, which was one of the first products Jobs launched after coming back. (And could be credited as the major turning point.) The iPod came out in 2001, along with the shift from the classic OS to OS X and launch of the iBook and an overall major product shift.

The iPhone was long after Apple was a majorly successful company that people wanted to emulate.

Microsoft also never just gave Apple money for no reason. They settled Apple Computer, Inc. v. Microsoft Corporation by agreeing to continue to develop Office for the Mac and to purchase $150M in non-voting Apple shares, and both companies agreed to cross-licensing of OS patents.

The iPhone came about 6 years after the iPod, which itself was wildly successful so certainly Apple was nowhere near bankruptcy when the iPhone launched.

They also weren't on the brink of bankruptcy when they made the iPod either - the original iPod launched in 2001 which was ~4 years after the Microsoft investment you mention (that happened in 1997).

Apple actually launched the highly successful iMac (the colourful ones) back in 1998, and it was arguably the success of that which restored Apple to having good profitable. I.e. it was already well on the 'up' by the time the iPod launched and propelled them to even greater financial success.

No those came later, it was the colored translucent iMacs that got them back in track, then the iPod.

There were a few years between those events.