When you said your friend was "with Apple". I also understood that to mean he was employed by Apple because that is the common English language usage of the word "with". When a person is said to be "with" a company, that generally means the person is employed by the company.
For reference, see definition #9 for the word "with" at Dictionary.com -
9. In the membership or employment of: plays with a jazz band; is with a publishing company.
As for my opinion of Mac OS 8 vs Windows 98 - Mac had the superior user interface. Windows had better multitasking. For me, a good user interface is the top priority.
There are a whole lot of def's for "With" at you link. You just picked the one that fit your needs. There are many others...such as:
Next to; alongside of: