Phil has an original iPad Pro and iPhone. Should he upgrade? Leo says that those are both still fine. But you may want to think about the M1 Mac. That's a huge shift. But don't buy it just yet. Apple does have an event in June for the Worldwide developers' conference, and Leo thinks there may be a new generation M1 chip. So keep your powder dry on buying a new Mac until June. But he's expecting a new iPad Pro this month with an A14X chip, the mobile version of the M1+. Also note, that the current MacBook Pro and the latest iPad Air both have the same chip.
Now is not really a good time to buy.