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Planning first India trip: Advice needed!!

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First, thanks to everyone taking the time out to read and possibly help me. I'm in the process of planning my first India trip and have tons of questions. I have done a lot of research but have not found satisfactory answers to the questions I will ask here. If you can help in any way, it is greatly appreciated, thanks in advance.

First, the basics. I plan to travel for roughly about a month and a half in India then head to Nepal for about two weeks. I will be traveling only around Northern India and am putting priority on spending more time in less places then seeing more places and spending less time in each. I will be traveling from the last week of December 2013 to mid/late February 2014. I will be on a pretty strict budget. I am a seasoned traveler and have no problem roughing it. Let me first lay out my tentative itinerary. My first question: can anyone recommend how many days I need to really get a feel for each place. I plan on spending anywhere between 2 and 5 days in each place:

Arrive in Delhi

Delhi to Amritsar

by road to Dharamsala

Fly to Delhi (SpiceJet)

Overnight train to Jaisalmer

by train to Osian

by train to Jodhpur

by train to Ajmer

by train to Udaipur + day excursion to Ranakpur + day excursion to Eklingji

by train to Jaipur

by train to Agra + day excursion to Fatehpur Sikri

by train to Gwalior

by train to Orccha

Orccha to Khajuraho

Khajuraho to Varanasi

On to Nepal.

My first priority is firming up where I will go and how I will travel. Is there anything on this list I should leave off? Anything I should add? Is it to ambitious for a month and a half? I know this is all pretty subjective about likes and dislikes? I am just hoping to get some input from people who have done a similar trip.

Next, I am assuming (minus the spicejet back to Dheli from Dharamsala) I will be traveling mostly by train. I understand this is the most cost effective way to travel and a cool part about the India experience. My question is how far in advance do I need to book my train tickets. I don't want to get stuck anywhere, but want to remain flexible with my time. If I arrive in a city, could I book a ticket 2 days in advance when I leave? Should I wait until I arrive in Dheli and book everything those first few days? I'm just a little confused on what the time table should be for booking trains.

On the same note, how far in advance should I look to book accommodations? In most of these places, could I arrive and find something open the same day, or should I book in advance? This question obviously ties in with my trains and when I will be arriving in each place?

Basically I think these two things come down to should I book my whole trip a few weeks in advance, should I book everything my first few days in Dheli before I set out, or should I just wing it and book as I go?

I know this is a lot, so I really appreciate the help. Any advice or input would be great. Thanks in advance!

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