I enjoyed reading your post. Many hobbyist black hat hackers and script kiddies are pretty lazy. I understand the concept of never connecting to a Starbucks WiFi to avoid a man-in-the-middle (MitM) attack it probably a bit unreasonable. Security is often like locking the front door of our home or our car door when we leave it unattended, and these are merely deterrents because most thieves are pretty lazy, they will walk around the mall pulling door handles until one opens so the deterrent is quite effective. The same idea often applies to network security, if we use something like a VPN to encrypt communication while far from unhackable it’s likely enough to have the individual perpetrating the man-in-the-middle attack pass over us and look for easier prey. In a world where our lives are conducted online, my personal philosophy is to lock the door of the house, and the car when I leave it unattended but never leaving the house or the car unattended is probably unreasonable.
If you’ve never seen how easy it is to conduct a MitM attack here is a good instructional video (https://www.youtube.com/watch?v=IdhuX4BEK6s) that shows how to use the WiFi Pineapple to carry out a MitM attack. Scary simple. 🙂 It’s much harder to crack the encrypted captured data so if someone is sitting at a Starbucks with a WiFi Pinnable conducting a MitM attack with either a rogue access point or by spoofing an access point (evil twin AP) the probability of the perpetrator spending the time to decrypt the data is low. A MitM attacker will likely move on to someone else who is passing unencrypted traffic.
Pfleeger, C. P., Pfleeger, S. L., & Margulies, J. (2015). Security in computing (5th ed.). Upper Saddle River: Prentice Hall.