Web Developer to help me Integrate MailChimp and/or Convert Kit for Automated Emails

I have a Spanish Tutoring business that is growing and I need help setting up automations to help free up more of my time. Here are the specific tasks I need help with: 1.) Using a better plug-in on my website to integrate MailChimp. Right now, when someone signs up for my mailing list, the form does not allow me to "tag" them before they come into MailChimp. So I currently have too many MailChimp Lists. I need to consolidate my contacts into one list but can't do that until I figure out how to "tag" new emails as they come in. 2.) I have a Basic Spanish course on Teachable that I want to launch in January using the Evergreen Model. Basically, I need it to have open/continuous enrollment but, in order to make that happen, I need to have automations set up. So, when someone purchases the course, I need them to be added to a list on MailChimp (or Convert Kit?). After that, they will receive a series of automated emails over 6 weeks. I have no experience with "Convert Kit" so I'm not sure if this is something I would need to make this happen. 3.) Lastly, the backend side of my website on WordPress just looks like it needs to general maintenance. So, I'm also looking to build a long-term working relationship with the right person to keep my WordPress site in tip-top shape! As well as someone to help me troubleshoot problems with my site.