@ Kenneth
RE: Update Failed: The update cannot be installed because we will be unable to copy some files. This is usually due to inconsistent file permissions.
That is a WordPress error. YOu’ll have to correct the file permissions in order so WordPress has the correct permissions to copy/overwrite files.
RE: I have made some mods in a few files.
If you modded files in the core Connections plugin, you will lose whatever mods you have made.
RE: Should I sftp to the plugins directory?
That is the only way I know of to recursively adjust folder file permissions. So, yes.
RE: Is there an order to upgrading? Upgrade the plugins first and then connections plugin?
Yes, you should first upgrade the core Connections plugin before upgrading any of it extensions. Just in case an extension requires a newer version of Connections that what is installed.
Hope that helps!
