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.