Combine - Select Into, with Insert Into Select
When the automation fires off the second time, I get an error because the table already exists and, consequently, the second round of data isn't inserted.


I would suggest you to put a condition to check the existence of the table

If exists (select 1 from sys.tables where name = '' and type = 'U')
begin -- table exists, so insert values in it
insert into table_name values ()
end
else
begin -- table does not exist, so create it
create table table_name (column datatype)
insert into table_name values ()
end


You can even use below sql to create new blank table as the where 1=0 will always be false.

Note that it wont create any indexes from old_table into new_table.

SELECT *
INTO new_table
FROM old_table where 1=0


To capture errors, you can use TRY/CATCH