I don't want to hear him sing the classics. I want to get used to his voice singing new Journey songs.
The thought of hearing Steve A sing the GH's terrified me at first. I bought Arrival and grew to like his voice long before I even considered purchasing the 2001 in LV DVD.
If he starts with any of the classics, he may as well still be in his cover band. He needs to establish himself as the lead singer for Journey with a few songs he can call his. After the fans get used to his voice, then it won't be so weird to hear him sing the hits.
But in answer to your question I'd want to eventually hear him sing "Escape" and "When You Love a Woman."