Upgrading from 1.9.19+ to 2.7

Hello, 

I usually try to avoid creating threads because much information can be found by searching existing ones but I was advised (by Guillermo Madero) here to add one of my own.  

We have Moodle 1.9.19+ running on Ubuntu 14.04 LTS, PHP 5.5.9-1ubuntu4.5, and Mysql 5.5.38.

We have several third party plugins and some of our own bespoke code.

I have already upgraded on a staging server from 1.9 to 2.2 then 2.5 then 2.7 and I have successfully re-established most of the "extras" .  I moved the 1.9 code to another directory (this is something I always do anyway for convenience, even though we have both local and remote tarred backups of the database, the moodle code and the uploaded data) and put the the "undefiled" moodle 2 code into the moodle directory and the upgrade process as I remember it went reasonably smoothly.  At the time of the first of these the server was running Ubuntu 12.04 so I suppose that difference might have created an issue?  I doubt it though.

The staging server (also Ubuntu 14.04 LTS, PHP 5.5.9-1ubuntu4.5, and Mysql 5.5.38) is running a restored version of our moodle database but due to lack of space it is missing almost all the uploaded data.  This is the key difference.  The uploaded data probably amounts to about 260GB since the tar file (which has code, database dump, and uploaded data) is 270GB

I attempted to upgrade the live site last week but the upgrade stalled very early.  Timeout I think.  I then restored back to 1.9 successfully.  I would rather not go through this cycle again as it was obviously time consuming but also quite nerve racking.

I have made some of the adjustments described by Paul Nijbakker (thread linked above), to whom thanks again.  The ones I didn't make were to the database and they are not needed in our case.

Now there are two main questions: 

1. Any further advice, anyone?
2. How have people found using the command line to do this?
   1. does it indicate progress?
      
   2. is it significantly quicker?