I agree with most of what's been said so far - As to automatic oiling, the Makita UC4030A has auto oiler and a 16" bar. I bought one for a similar project, it's pretty highly rated. I plan to use a flex mount, tie the trigger on (it also has soft start) and stick to vertical cuts, with the last couple feet of extension on a hinged joint supported by a webbing strap so the saw cuts mainly with gravity. I'll start/stop the saw with one of those plug-in switches you can buy at Home Depot, Lowes, etc.
Looking at two 10 foot sections, small hydraulic cylinders limited by a flow control needle valve to slow down, mounted either on front or rear buckets of my 580B. I will use all 2" receivers and tubing for various configurations. That will give total extension from ground anywhere from 30-40 feet.
Hope to have it done by spring, no pix yet... Steve