Rohit's Group Adventure Trips

Hi, I'm originally from India but living in the US for the past 10 years so feel more at home here :-) Quitting my job now and taking a break in India for a few months. Want to do a month long road trip all over India. A tentative itinerary is:
Delhi-Jaipur-Ajmer-Jodhpur-Udaipur-Ahmedabad-Surat-Aurangabad-Bombay-Goa-Bangalore-Mysore-Kozhikode-Kochi-Thiruvananthpuram-southern most tip of India- Madurai-Chennai-Hyderabad-Visakhapatnam-Bhubaneswar-Calcutta-Varanasi-Agra-Delhi. 23 cities in 25 days. I'm also planning a second 6 day leg north of Delhi. Delhi-Amritsar-Dalhousie-Dharamsala-Shimla-Chandigarh-Delhi

I'll be renting a vehicle (probably a SUV) for the road trip and driving it myself ; unless someone wants to volunteer and take on the Indian roads :-)

The approximate cost for the trip would come out to be $2-3 k per person including food/gas/boarding/car rent. Its a tight budget and I'm not looking for anything more than safe and healthy amenities.

I'm looking to do the trip in June but am pretty flexible - could be May. However, July-Sept is the monsoon season and it will be difficult to drive in that season with road closures, flooding, landslides and the like.