1) I can have two listeners on same port that 1521 (Verified after testing).
Both the listener are up and running.
2) The issue was as below and it's strange:
Windows 2008R2 has new interface like commandprompt and it is windows power shell. I was setting ORACLE_SID first and was logging into the database. But "ENVIRNMENT CANNOT BE SET IN THIS WINDOWS POWER SHELL". Then I did it from normal windows command prompt and it could set the env veriables to logg into the proper db.