Issue upgrading from 1.0 to 1.6

I'm working on upgrading to 1.6 in order to take advantage of the security update but the upgrade process from version 1.0 to 1.6 isn't going well for me. The database updates don't complete successfully. Here's the output I'm getting using Drush:

$ drush updb -y

 Office_hours  7100  Change value of 'day' column from 0-13 range to normal 0-6 
                     day range.   This allows for more then 2 hours blocks per  
                     day.                                                       
 Office_hours  7101  Add a Comment column.
Do you wish to run all pending updates? (y/n): y
SQLSTATE[42S22]: Column not found: 1054 Unknown column                   [error]
'field_hours_comment' in 'field list'
Performed update: office_hours_update_7100                                  [ok]

'all' cache was cleared.                                               [success]
Finished performing updates.                                                [ok]

The updates don't actually complete because the additional column in update 7101 isn't actually added. If I run drush updb -y again, the output is exactly the same.

Also, when viewing the field data in the admin, it appears as if the information on certain days has been lost. I'm attaching a couple of screenshots (before and after).

BEFORE (v 1.0):

AFTER (v 1.6):

Also, when attempting to save a node with an office hours field on it I'm getting the following PDO error:

PDOException: SQLSTATE[42S22]: Column not found: 1054 Unknown column 'field_hours_comment' in 'field list': INSERT INTO {field_data_field_hours} (entity_type, entity_id, revision_id, bundle, delta, language, field_hours_day, field_hours_starthours, field_hours_endhours, field_hours_comment) VALUES (:db_insert_placeholder_0, :db_insert_placeholder_1, :db_insert_placeholder_2, :db_insert_placeholder_3, :db_insert_placeholder_4, :db_insert_placeholder_5, :db_insert_placeholder_6, :db_insert_placeholder_7, :db_insert_placeholder_8, :db_insert_placeholder_9), (:db_insert_placeholder_10, :db_insert_placeholder_11, :db_insert_placeholder_12, :db_insert_placeholder_13, :db_insert_placeholder_14, ...

Any ideas what might be causing all of this? Thanks!