"Free" wi-fi means coffee shops, 7-11's, and McDonald's, wherever T Mobile has an agreement with a provider. Problem is, they aren't convenient and they aren't private, so I look at it this way:

Emergency Situation: I'll make a phone call, no matter how much it costs.

Casual Family Connections: We all will use iMessage, it costs nothing at all except a tiny amount of data (we don't text photos or videos) and on a two-week trip to Asia I'll send/receive around 1000 texts I'd guess. Again, iMessage is a free texting service from Apple, so unless you have friends/family on non iOS product you don't need an expensive texting plan or data plan from your provider.

Daily Family Video Chat: I'll do it from my hotel room (or my corporate offices) and do it on Skype between PC's as its best for a bigger group.

Occasional Private Chat: My son will text me, I'll tell him I'm in my hotel room on wi-fi, he'll FaceTime me, tell me he needs me to loan him money for video game.

So, yes, you'll be doing your video chats from your hotel room's wi-fi connection as its stable and private. You can use an iPad for that purpose, but its hard to have a conversation with a group of people because on their end, without a stand to put the iPad on, it's hard for all of them to gather around such a tiny screen. Therefore, consider Skype going PC-to-PC.

BJ