I want to be able to tow a open car carrier and tow a vintage VW Bug on it to car shows and was wondering how these trucks handle that ?

Was thinking of a 14 or 16 foot carrier

I have a 1997 4x4 reg Cab with a 4.0 in it.
98 K on the engine and Automatic.

I also was thinking of getting a trailer hitch system for it
and was also wondering will I need the trailer breaking system as well?
oh so many Questions

Thanks for any advise!

Jeff