I travel so much and as a result naturally have to address the many issues that can get in the way of "staying connected" while on the road. The biggest one has always been reliable cell coverage in hotel rooms, especially when I'm in a high-rise hotel that hasn't installed a neutral or carrier specific DAS system. The DAS allows for the cellular coverage to be extended, which is why at airports Boingo's other business, that of operating DAS systems is so important to travelers of all types.
The second is reliable broadband. One that not only downloads fast, but uploads fast as well and is free of any port blocking, deep packet inspection or firewalls that disrupt real time communications.
Recently though, I ran into the most hilarious and serious condition of all. I was staying in an AT&T Wi-Fi powered hotel (formerly called SuperClick) the hip Hotel Indigo in San Diego when I realized that not only was my cell coverage on both AT&T and T-Mobile powered iPhones poor, but that while they were both connected to the Wi-Fi network, neither of them had Wi-Fi calling working.
My call to AT&T Wi-Fi support, yielded no support as they put the burden on AT&T Wireless. AT&T Wireless support were clueless as to why it wouldn't be working (ironically the same phones on another AT&T Wi-Fi/SuperClick property in Miami worked perfectly for both operators on the 32nd floor of the Intercontinental.) They promised to look into the matter but two weeks later, no one has called. What's worse is I sent a LinkedIn message to the former CEO of SuperClick who now works for AT&T --no reply, as I wanted comments before I penned this. On the other hand, a friend at T-Mobile was very interested in hearing that an AT&T Wi-Fi powered hotel was blocking their traffic, comparing it to the situation at the Opryland Hotel and Conference Center were Marriott was blocking third party Mi-Fi's from working. And we all know what kind of fine that levied.
Oh, and as for being connected. My Verizon LTE coverage was good, not great, but at least I could place and receive phone calls. That's why I call the game "Cell Phone Roulette" When you're in a hotel. You never know which mobile operator will work or not.