[g105b]

I know this is slightly off topic from OP's question, but I'm chiming in with one piece of first-hand advice:

You can self host mail alongside gmail/outlook on your own domain. More than one email service can run concurrently, without any problems.

That often overlooked fact allows you to quickly set up something like gmail on your domain, then use the trial period to see if you can self-host with any success. If you can, then you can shut down the trial, or move on to trial another paid service like 365 while you're still "trialing" your own host.

It really helped me make the transition.