Updated Jarvis's words.

config/templates/speech/daily_briefing.yaml

@@ -310,9 +310,14 @@
 
 
           {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') < as_timestamp(now()) %}
-            {{ [ 'Today is a school day.',
+            {% if is_state('sensor.school_start_days2go', '0') %}
-              'It is a school day. '
+              Today is the first day of school! There are {{ states('sensor.school_end_days2go') }} to go until the last day.
-            ] | random }}
+            {% else %}
+              {{ [ 'Today is a school day.',
+                'Skylar has school today.',
+                'It is a school day. '
+              ] | random }}
+            {% endif %}
             <s>Pickup today will be at {{(state_attr('input_datetime.school_day_end', 'timestamp') | int | timestamp_custom('%I:%M %p', False)) }}</s>
             {% if 'Digital Learning' in states('sensor.school_event') %}
               But it is a digital learning day so the commute will be short.

config/templates/speech/morning_wakeup_report.yaml

@@ -93,9 +93,13 @@
     <p>
       
     {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') < as_timestamp(now()) %}
-      {{ [ 'Today is a school day.',
+      {% if is_state('sensor.school_start_days2go', '0') %}
-        'It is a school day. '
+          Today is the first day of school! 
-      ] | random }}
+        {% else %}
+          {{ [ 'Today is a school day.',
+            'It is a school day. '
+          ] | random }}
+        {% endif %}
       <s>Pickup today will be at {{(state_attr('input_datetime.school_day_end', 'timestamp') | int | timestamp_custom('%I:%M %p', False)) }}</s>
       {% if 'Digital Learning' in states('sensor.school_event') %}
         But it is a digital learning day so the commute will be short.
@@ -107,7 +111,7 @@
         But today is the last day of School! 
       {%- endif %}
     {% endif %}
-    {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') < as_timestamp(now()) %}
+    {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') < as_timestamp(now()) and 'Digital Learning' not in states('sensor.school_event') %}
       {% if is_state('sensor.school_lunch', 'Nothing') %}
         I am not sure what the school menu is for today, so plan on Skylar taking his lunch 
       {% else %}

config/templates/speech/skylar_morning_briefing.yaml

@@ -58,9 +58,13 @@
 
     <p>
       {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') > as_timestamp(now()) %}
-        {{ [ 'Today is a school day.',
+        {% if is_state('sensor.school_start_days2go', '0') %}
-          'It is a school day. '
+          Today is the first day of school! 
-        ] | random }}
+        {% else %}
+          {{ [ 'Today is a school day.',
+            'It is a school day. '
+          ] | random }}
+        {% endif %}
         <s>Pickup today will be at {{(state_attr('input_datetime.school_day_end', 'timestamp') | int | timestamp_custom('%I:%M %p', False)) }}</s>
         {% if 'Digital Learning' in states('sensor.school_event') %}
           But it is a digital learning day so the commute will be short.
@@ -91,7 +95,7 @@
       </p>
       
       <p>
-        {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') > as_timestamp(now()) %}
+        {% if is_state('input_boolean.school_today', 'on') and state_attr('input_datetime.school_day_end', 'timestamp') > as_timestamp(now()) and 'Digital Learning' not in states('sensor.school_event') %}
           {% if states.sensor.school_lunch.state == 'Nothing' %}
             I am not sure what is on the school menu today, so You may want to take your own lunch today. 
           {% else %}