Может быть, что-то вроде этого:
EntityTracker.find(:all,
:from => 'entity_trackers et',
:select => 'COUNT(et.id) AS count',
:conditions => ['et.action = ? AND
et.type_track = ? AND
et.date > (SELECT MAX(ua.date)
FROM user_actions ua
WHERE ua.entity_id=et.entity_id AND
ua.type_action=et.type_track) AND
EXISTS (SELECT questions.id
FROM questions
WHERE questions.id=et.entity_id AND
questions.user_id=?)',
'ANSWERED', 'QUESTION', user_id])