1-What kind of welding machine you got in mind?
2-Its a one way trip (you need to be concerned with how many Amps you can get through your cable)
3-Yes. Secondary voltage is less than 100V (hope you dont need much more than 30V)
4-Open-circut" generaly refers to GMAW (Mig) but you wont find many Mig guns longer than 25 feet.