1) I generally agree with the first argument, but I think context matters a lot. There’s always a market price depending on what the product does and what competitors offer. If your pricing is far below or far above that range, it usually won’t work out well. Our add-on was mostly for 1-3 ppl team.

2) As for the second point that’s definitely a lesson I keep bumping into and somehow never fully learn. No matter how clearly you communicate and give advance notice, users still perceive it negatively. And yet, as a user myself, I regularly get emails from services I pay for about price increases or plan changes. Very few companies offer true grandfathering forever.