I lease an apartment in Belmont heights and with the owners permission I sub lease it on Airbnb.

Question #2, If I do allow my tenant to take in a new roommate, I am thinking it best to have him set up a sublease situation with my permission so that I do not have to deal with the new renter, the current renter would be responsible for arranging all communication with them, however I would provide a lease and ensure that I am 100% comfortable with the conditions that he is setting with the new renter.

It is the responsibility of each resident to obtain their own insurance coverage.No one shall change the color of the walls unless permission is obtained from Lake time investing.

At least one neighborhood here will not let you cut dead trees or ugly bushes without permission. 

Every co-op that I have looked at (and owned) had rules against, where you needed to have permission to rent and it couldn't be more than one or two years total in the time that you own.

The second restriction was due to the previous seller not getting the other owner's permission to sell.

It also allows permissions for users who can't see income.

It appears that you are in Volusia County, Florida, if the property had been granted a tax exemption as Homestead property, that tax exepmtion will also become a court decision before permission for sale is granted to the Personal Represntative.  

Had no clue on how to start it, do I need a permission?

He replied that the tenant gave permission.