Hey @Fused_Integrated_Mar,
The settings are preserved when an extension is re-installed however I’d highly recommend that you create a staging site. This is very useful because you can test drive any X or Pro updates in the staging area, do the customization and troubleshooting without disrupting your live site. Once everything is perfect, you can easily and flawlessly proceed the update in the live site. To know how to create a staging area, please check out these articles:
http://www.wpbeginner.com/wp-tutorials/how-to-create-staging-environment-for-a-wordpress-site/, https://maintainn.com/2015/02/how-to-create-a-staging-site-for-wordpress/
Taking a complete backup before any update is a best practice too so make sure to take a backup of your site.
After doing the updates, always remember to clear all caches (if you are using WP Rocket, WP SuperCache or W3 Total Cache) when updating so that the code from the latest release is always in use. This will help you to avoid any potential errors.
Hope this helps.