Whitelisting system emails

It seems inappropriate to consistently tell our clients to check spam, or whitelist IP addresses, in order for Dear system emails to reach their intended recipient. And even when this is done, emails to new contacts still get lost, or reply emails still get stuck in the next recipients spam. There needs to be a more global approach to fixing this. We switched from Xero, and they have managed to overcome the problem for all of their users, can this be investigated within Dear too please?  Thank you.