So I realized my itinerary suffers from two isses: it is too ambitious and structured, and I did not take into account the Indian summer.
For one thing, I will not be visiting most of India, because I don't think it will be enjoyable at all in 110 degree weather. This is the advice I got from all of the Indian people I have spoken to. I may still include some of the mountainous and Northern parts in my journey, where the temperatures are cooler. This may include Ladakh, Leh, Sikkim, Darjeeling, and Dharamsala.
Other Northern areas I might include are Nepal and Mongolia/Beijing. Tibet seems to be a hassle to get into. I expect this northern part of the trip to take 30-40 days.
The other part of the trip, I will choose either Indochina (Thailand, Laos, Cambodia, maybe Vietnam) or Indonesia. Basically I won't have more than 30 days to do these parts so I won't be going in with a set itinerary - only the necessary Visas and I'll wing it from there.