When starting out with simple tasks, get a task to work with the assistant. Then copy it and open the front panel to convert it to a VI and poke around in the Block Diagram. Basically ready-made example code for your simple application which will help you understand how to make more complex operations.
Yes
No
Use a DAQ Assistant (1 for each device) in a loop. Its a beginners friend (and sometimes advanced users). It automatically sets up things for you so you don't have to worry about starting and stopping every loop. If possible write to the whole port at the same time.
Hint:
The previous solution is probably better than mine, but I can think of an alternate way. Fonts are installed in Windows in the following path %windir%\fonts You can probably perform a list files finding all installed fonts there. I'm not sure if fonts can be installed into a location other than that, and if it can then that is a reason the .Net method might be preferred.