LearnDash Customisation potentially server work

Hi, I am using Wordpress and LearnDash with a couple of Plugins (such as WooCommerce and WooCommerce Subscription) on a VPS. Everything should be working fine, however, some things don't work. And this is where I need your help. 1. LearnDash has a plugin that allows emails to be sent to students (LearnDash Notifications) when e.g. an assignment has been uploaded. I have installed it and set it up, unfortunately, it doesn't work. It might be because on my VPS, PHP triggered emails don't work at all. I have worked around this by adding a plugin that sends Wordpress emails via Gmail, but at least for these notifications, it doesn't seem to work. So it might have to do with the VPS and you might have to fix something on the server without breaking it, or check if the issue is caused in Wordpress and fix it. 2. Trainers should have access to the Wordpress Backend and be able to rate and comment student's assignments. I tested with two themes (we are using Academy theme, but I tried with a default theme too). Both times, the trainer doesn't have access to the backend but gets redirected to his profile page upon login. This would need to be fixed too. So the trainer would need to be able to login with access to the backend and be able to rate and comment the learner's assignment. As I am not a very technical person, I will need support in the future as the business grows, so please consider this as some sort of "application" for an ongoing relationship. Budget is 45 € For questions please don't hesitate to ask. Kind regards,