I am attempting to use WhenAnyObservable for the first time.
When a ReactiveList Count == 0 and a tipText length is > 0 then I want to set a local value to true in
You've got the right idea, but WhenAnyObservable doesn't return items until it has an initial item for both "sides" if you use >1 Observables. So you probably want:
this.ViewModel.WhenAnyObservable(
x => x.AutoCompleteItems.CountChanged.StartWith(0),
x => x.WhenAnyValue(y => y.TipText),
(countChanged, tipText) => countChanged == 0 && tipText.Length > 0);