1) MacBook Pro 16 inch ?
2) MacBook Air with new Intel Processor ?
3) New AirPods - IP68 ?

And that's a lot of question mark to start with.

Definitely Macbook Pro 16" will be unveiled.
New Ipad Pro 2019 maybe?
not gonna see new Macbook Air as Apple already upgraded it earlier this year with brighter screen (500nits vs last year's 400)

Hopefully price further drop

16 Inch will be New Model, very rare occasion when Apple introduce new Model with a price drop. Well in a matter of fact that also applies to any brand when they introduce new stuff.

The other items that was never really have the upgrades are iMac apart from being slim but thats about it no more new design for years on end. Was it 2012 model that is ?

I think iPad Pro 2019 and a Macbook.

Did you mean MAC ..
Always wanted to see a round MAC instead of the normal Square version.

Sorry...yes. I mean MacBook Pro.

There is one more announcement that's due for October and that is Catalina OS.

Was not announce in September.

Apple device with its own ARM processor well that's really is an eye opener for a change .