Hi,
Thanks for contacting us here about this extension.
If I purchase the $29.00 option and WP media folder updates in 2019 will I have to pay for the update?
When your subscription is expired, you should renew to update new features.
For more information:
https://www.joomunited.com/features-and-integrations-faq/how-does-membership-renew-and-billing-working-on-joomunited Is there a version where I automatically get updates for 5 years?
I'm sorry, we have only packages for 6 months and a year. If you need to deal with a longer subscription with 20-30% OFF, please, drop us a billing ticket (Menu > Ticket support > Billing - General questions).
Hope it helps!
Cheers,