Training Communication

For training communication you need an NPC you can steal from and not get attacked. There are a few like this, but the one that is best is Milano Calzone. If you make him neutral you don't lose any vendors, since Don Barlone is still friendly.

Go to Milano and pickpocket him untill he catches you. Then threaten him, and talk friendly to him. That will train communication, and sometimes you will see communication go up. Now rest for 24 hours. Now you can threaten and talk friendly again. Repeat this untill you max communication ( gonna take a LONG time ).

After a while Milano will go neutral ( unless you don't use threaten ), but I've never seen him go hostile. - TinyMage