Greetings Wheels
First, let me offer the suggestion of using amateur radio (Ham) as a comms option. I question the effectiveness of the CB and FRS radios in the urban enviroment, mostly because of lack of range and power. Most amateur repeaters in the urban areas have a large footprint and afford more reliable communications than does the citizens band equipment. I have noticed that an increasing number of professional drivers have switched over to the amateur bands due to previously stated reasons and the conversations are by and large "G" rated, as opposed to some less regulated bands.
Secondly, 1+ on the two cell phones on different networks. I've had to do that for several years due to coverage problems in parts of NC / SC / GA where I travel.
Sounds like you have the rest of the bases covered. In reference to the winter weather, better you than me. If I never see anything white on the ground other than warm Caribbean sand I'll be extremely happy.