Problems inserting timestampz field

I am new postgres/timescale.

I am having trouble inserting timestampz values.

i have checked the db TZ …

SELECT current_setting('TIMEZONE');
 current_setting
-----------------
 America/Toronto
(1 row)

When i formatted my datetimes with or without timezones, i am getting some weird inserts
and duplicate key errors when the Timestampz fields do insert properly

for example, with times having timezone appended;

continued…

more strange,
with the table empty (no rows) and the same insert without timezone appended;

While the first method inserts the dates for this small amount of rows, (with altered TZs),
eventually i get duplicate key error when inserting lots of data and using dates with appended timezones

Can anybody suggest what i am doing wrong here?