While I agree with your first sentence, Boris doesn't appear to have made any efforts to understand non-rich life - although he clearly has made himself electable so could well have made such efforts and publicised them in outer London, just not inner London.
Or more succintly: I don't oppose him for being a post Tory prat, just for being a prat.

Some years ago I found that among all my friends (aged 25-30ish), I and one other were the only ones never to have been made redundant and thus gone on the dole, and that was because we were doing PhDs and never had jobs to become redundant from. I think both of us had claimed benefit previously. I don't know how representative that is, though, given I don't know a single Boris voter...