For the most part, upgrades tend to be from the admin CP. However there will be occasions, such as large upgrades like this, where file upload is required to upgrade
We would not do upgrades on your behalf on a self hosted environment. The $199 a year is what you pay for continued updates on your software, and IPS support and services.
We agree! We created a cloud based product just for that reason. Feel free to reach out if you would rather not have to deal with hosting of the platform, and would like to convert over to our cloud platform.