The plan so far

It might be worth starting with what the plan is so far, and see how much it changes even before taking off on the first flight:

April 9th-11th: Fly to Kochi, India
April 15-30th: Go travel somewhere in India by train
May 5th: Fly to Istanbul, Turkey via Doha, Qatar
May 6th-14th: Loop from Istanbul down to Try and Izmir back to Istanbul
May 14th-16th: Take the ferry to Odessa, Ukraine (originally planned train through Bulgaria and Romania, but this route should mean one less visa)
May 16th-22nd: Tour Ukraine via Kiev and Lviv, plus perhaps Yalta if there is time.
May 22nd-29th: Take the train to Budapest, then hop through Bratislava and arrive in Trebic, Czech Republic.
June 1st-10th: Travel by train through Krakow, Warsaw in Poland; Vilnius, Lithuania; and Riga, Latvia, then arrive in Tallinn, Estonia.
June 10th-15th: Find either a ferry (perhaps via Helsinki), bus, or train to St. Petersburg, Russia.
June 15th-July 7th: After a few days each in St. Petersburg and Moscow, take the train to Vladivostok, with possible break stops in Kazan, Yekaterinburg, Novosibirsk/Tomsk, Krasnoyarsk, Ulan-Ude/Baikal, and Khabarovsk.
July 10th - September 10th: Enter China via train to Harbin or Shenyang, then take time traveling down China with possible stops in Datong, Shandong/Taishan, and Guilin.
September 10th - September 30th: Cross the border into Vietnam, starting with a bus or train to Hanoi and perhaps Dien Bien Phu. Take the reunification express down through Hue and arrive in Saigon.
October 1st-30th: Get through or around Cambodia and into Thailand, then take the train down the peninsula through Malaysia and arrive in Singapore.
November 1st-30th: Hop down to Indonesia and figure some way of seeing as many islands as possible in a month.
December 1st - January 15th: Fly to Darwin, Australia, and try to hire a car to drive over to the East Coast, past Whitsunday Island, try diving the Great Barrier Reef, then cruise down along the coast to Melbourne. If there is time, continue to Adelaide and look up the cave diving there.
January 15th: Even by now I am assuming way to many things could change, not the least of which being that I might find an opportunity in the market to get back to work and start applying what I learned in Eurasia. If the S&P 500 has continued its current trend and is still below 400-600, this might be a good time to fly to India, drop off the then-2-year-old, then hop down to Capetown and work our way overland to Cairo, making it there by northern summer to go back and meet the points we missed in Central Asia.

Yesterday I started with the "consulate run" up Madison avenue stopping in consulates of some of this countries to find out about Visas. So far the most challenging one still seems to be Russia, and the fact that China and beyond will have to be applied for on the road...