Having said that my question is...... If I'm boon docking and use my wingard antenna will I be able to receive signal/free tv? And if I'm at an RV park that offers cable will I have to upgrade my existing tv (in the trailer) to a smart tv in order to watch local channels?
Absolutely not at least on a flat panel TV.
I have a smart TV and three dumb flat panels! Two of them are in my trailer- the smart one and another. Basically a smart TV is one that provides connectivity and computer-likefeatures-- playing video/audio files, internet, etc. The TV part is really no different from any flat panel.
It is true that there is a shift in frequencies for the new digital broadcasts. The batwing with the HD (Nose) added is an excellent antenna; however, it was tuned to the older frequencies. You can make a simple upgrade by getting the Razor retro kit as it uses the same crank and bar system that the batwing uses.