SES: Cheap & DIY & somewhat time intensive & Ok but not great delivery. Add dedicated IP for like $60/mo and you’ll get into pretty good to great delivery

Sendgrid / Mailgun: DIY & somewhat costly & pretty good delivery

ConvertKit: $100-150/mo for you current list. Focused on creators. Some marketing automation. They use a third party like Sendgrid but they manage everything. Fantastic to mediocre results. Fairly responsive team. Least labor requirement.

Keys to success DMARC. CFL participation. Problem with CFL participation, some of the big guys (like Comcast) won’t let small ships into the system. CFL essential to catching “Spam” button events to unsubscribe and not destroy your sender reputation.

Then there’s the whole spam control monoculture/cartel of BrightWorks / Symantec et.Al. Misbehave with one of their customers and you’re fucked for all their customers.

What benefit do I get from using those services, over putting an open source solution on a $5/month machine and using that?

This one has 8k stars on Github:

https://github.com/knadh/listmonk

This one also seems to be popular:

https://github.com/phpList/phplist3