Question: Where are you installing your EMS? If it is installed at the pedestal and then you are adding 55' of cords downstream, then you really don't know what the voltage is at the AC unit. Hopefully you have it installed downstream of your cords as close to the trailer as possible in order to get true voltage being applied to the trailer.
Most everyone will probably disagree, but if you are seeing the voltage drop to 109 at the trailer with only the AC load, that's nearly 9% drop over the "standard" of 120 and indicates to me your 30A service is significantly undersized. I wouldn't run an AC or refrigerator on this service.
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