首先使用compare bySeries.shift和chain mask过滤第一个连续值，并过滤所有没有Work in progress...值的行：
df = df[(df['Message'].shift() != df['Message']) | (df['Message'] != 'Work in progress...')]
print (df)
Timestamp Message
0 2018-01-02 03:00:00 Message received.
1 2018-01-02 11:00:00 Sending...
2 2018-01-03 04:00:00 Sending...
3 2018-01-04 11:00:00 Sending...
4 2018-01-04 16:00:00 Work in progress...
6 2018-01-05 05:00:00 Message received.
7 2018-01-05 11:00:00 Sending...
8 2018-01-05 17:00:00 Sending...
9 2018-01-06 02:00:00 Work in progress...
10 2018-01-06 14:00:00 Message received.
11 2018-01-07 07:00:00 Sending...
12 2018-01-07 20:00:00 Sending...
13 2018-01-08 01:00:00 Sending...
14 2018-01-08 02:00:00 Work in progress...
17 2018-01-10 03:00:00 Message received.
18 2018-01-10 09:00:00 Sending...
19 2018-01-10 14:00:00 Sending...
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