I'm interested in running a game on Skype for my fragmented old gaming group. As it's Pathfinder, my biggest hurdle seems to be the mapping. I'm not the sharpest dice in the bag and I was wondering if anyone knew of the most idiot friendly method of mapping for an online game. Doesn't need to be fancy or 3-d, just an easy way to keep track of characters and stuff for fights. Any assistance would be greatly appreciated.
Our group has been using Roll20 for 2 years now. It's free (though you can pay a subscription fee for fancier widgets), web-based (so no client to install), has built-in Pathfinder PRD support (as well as the D&D 5E SRD) and has both a built-in video/audio chat client or you can run it from within Google hangouts. (You can also forgo both and use Skype in a separate window if that's your preference.)
Mapping can be done by either drawing on the map with the built-in tools (though don't expect anything super fancy) or by dragging and dropping an image file from another source. It has a bit of a learning curve (though their wiki is pretty helpful) but pretty easy to use once you get the hang of it.
Roll20 is what our group uses when we can't all meet in meatspace. It's "okay," and for the price is quite good. I can't agree with the "pretty easy to use" characterization -- I could drink a bottle of ink and pee better user-interface code -- but it will get the job done.
We hang an iPad from the chandelier over the table and map for the player that moved out of state. He has yet to make a swashbuckler, however.
They hang 2 clothes hangers from the dining room table light, and place the tablet horizontally between the 2 clothes hangers.
I found the Roll20 interface pretty easy to understand and use. We have people in Colorado, California and multiple cities in Michigan in our group.
There's a lot of power there, even in the free version. You can set up different maps for different scenes, and there's a fair amount of free imagery to create more than the white hex/square base.
But you can use is just as a whiteboard, drawing lines and circles as the game progresses if you don't want to create a map before the game.
Some people use the camera video, some use a microphone/headset combo, and there's always the chat to fall back on if something technical fails.
The char sheets have built in macros and you can also write your own.
Overall easy to get started (but do go through the tutorial) and easy to add material to. The wikis are very very good.
I'd recommend using Discord for voice but otherwise everything Crystal said about roll20 is spot on...though finding tokens to represent things with its search engine is a pain at times.