Thanks everybody for the feedback!

I did purchase a cloud plan from joplin directly, and it worked with all my devices instantly, no fuss.

Linode had advertised a “one-click” solution to get NextCloud up and running, but it was far from it. A couple folks linked a GitHub page with a list of NextCloud providers and I decided on Cloudamo, and that was way more up my alley then Linode. No ssh, no console, no installs, just easy GUI. I am just waiting on the nameserver change and then hopefully I am good to go there.

It sounds like hosting my own email is not a good idea. I already have a proton account that I am using for email. I tried using it for File storage, but it has been lacking, and others have been unable to view or download what I share with them. Does anyone have an opinion on if Skiff is better enough to switch over? Could Skiff pages replace Joplin? Someone mentioned lack of security with NextCloud. Would you recommend Skiff Drive over it?

I will DM some of you for some advice on my local setup.