Welcome to the forum.
It probably helps to break the journey down into smaller sections
Tharwa to Thredbo about 10 days, mainly flat.
Thredbo to Hotham about 15 days plus side trips.
I'd allow one night at Thredbo and another at Glen Willis Retreat
http://www.glenwills.com/This is certainly part of the trip. I did two days in one long day and got to Glen Willis Retreat a day early, two days of bliss, washing and sleeping.
The weather for October-November could be anything. A few years ago in mid-October I was stuck in a hut for three nights - snow, a blizzard and raging creeks. At Schlink Pass I could not go over the Main Range - too much snow.
After Tin Mine Huts it's a nice climb to Pilot, from where you can go down the somewhat scrubby south side or take the west slope back to the road. Cobberas is probably best accessed from Cowombat Flat; someone else can give details. The time depends on your fitness, scrub and weather, all unknowns. Allow a day or so. You may have to carry water.
A GPS is useful on some untracked sections. A PLB is regarded by many as essential. A sat phone ... do not know.
Food drops should be at about 5-10 day intervals. This may be a starting point.
Kiandra
Thredbo, held at your accommodation
Glen Willis Retreat
A number of Victorian roads are closed until the Thursday before Cup Day, so you may need to put in some of these before winter. You should be able to mail food drops to Thredbo and Glen Willis. Fuel cannot legally be posted.
In the Jagungal region it's possible to take many ways to get to Schlink Pass. Most are off tracks. If you get to Cesjacks you can climb Jagungal as a day trip. Going south to Tin Hut, keep in the frost hollows above the Doubtful. This is much nicer than a road bash to Mackays, Grey Mare and Schlink Hilton, or the scrub on the ridge. There's less climbing too.
Camp at Cotter Gap and get across the catchment in a day. I reached Oldfields Hut for lunch, and dinner.
I had a very long, hot tiring day getting to Johnnys Top. I suggest camping at Buenba Hut site or Corner Creek.
Morass Creek is nasty, slime.
It's a long, hard day from Mount Wills Hut to the top of T Spur, with no water after the first two hours, small soaks at the bottom of Long Spur.
Big River should be okay at T Spur. Another option is to go over Bogong and down Quartz Ridge. The original Alpine Walking Track had this as a formal variation, so diverting a bit here or in Kosciuszko is okay and if the weather permits, much better.