answer Regarding Question 2 :
if u have 50-60 test case in single .robot file .
Than u can use test setup in setting , this test setup will run first before all test case .
and put the checkin inside the code in keyword of test setup .
like :
*** Settings ***
# By Default, Connect_To_Collector Run Before all Test cases
Test Setup verify_user_login
***Keywords***
verify_user_login
IF '${loginDetails}' != ' user logs details' fail
may be it will help !!
Regards,
Sidharth Raj