I misread the comic initially as "fancier phone FOR $500" and was feeling very, "Dammit, Tilly!" till I reread it. Then I was more, "Dammit, Tilly!" in a good way.
For the posts about Tilly's work damaging entry level employees, definitely possible but I'd be hopeful that Tilly would be able to quickly get access to higher ups with the type of authority to okay those deals. In my experience, depending on the level you are/are dealing with, there is a hard line in what they can actually do, no matter how persistent the customer is being. Although that doesn't mean the higher up won't get into trouble either.