Your first step here should probably be to fire up a $5 droplet at DigitalOcean and give the install a shot. You will be able to run multiple plugins and make mistakes with little to no risk. Pretty quickly you’re going to learn if self-hosting is for you, and if not have some idea of how much you’re willing to pay others to do it.
That $5 is prorated, so if you decide after 24hrs the exercise was a mistake you’re going to be out of pocket to the tune of… $0.16
Mailgun will be free below 10k emails/month as long as you don’t do anything daft, it’s very low-risk and will help you learn about the platform as you go.