While I am not that enthusiastic about either of these 2, I would personally choose WP Courseware over LearnPress almost solely based off of the negative LearnPress reviews. A learning management system will be a core part of your website and you are going to want to choose a solid solution from a reputable company. My main issues with WP Courseware are that it requires you to have a separate e-commerce and membership solution in place. That is 3 different systems, 3 different learning curves, and 3 potential things and can go wrong, no thank you.
LearnPress Vs WP Courseware 2019
LearnPress is a comprehensive WordPress LMS Plugin for WordPress. The core plugin is free and there are many free extensions and paid extensions available.
WP Courseware allows you to have online courses on your WordPress website. It’s a solution ideal for people that already have an e-commerce platform and a membership plugin and just want to add courses.