About the logistics of doing your thing in India and Nepal, there are the following considerations. You would travel to India on a tourist visa, which limits your stay for a maximum of 180 days for one entry (visa starts counting from first day of issue, not from first day of entering the country). If you happen to be a U.S. citizen, you can apply for a ten-year-visa which gives you the right to enter India for 20 times 180 day-stays in sequence, but you need to leave at the latest on each 180th day, for instance to Nepal, entering which costs you 25 US Dollars each time for 15 days stay, 40 for a month, or 100 for 3 months.
If you are not an American, you have to go the way of ordinary mortals, and apply for 6-months-visas for India each time you need to leave. Your best option in such circumstances is to stay in India for 6 months, then migrate to Nepal vor 150 days (max allowed stay in Nepal), then apply for India visa again, and stay in India again. Visas always cost money, though, and you cannot do without. Visa issuing changes from time to time. You might be asked to go to your home-country to apply for a 6-month-visa, and be given only 3 months.
Most Theravada Buddhist monks use money in India. India does not understand the tradition of Pindapat anymore. You won't get food from anyone, except if you educate them.
You could do your thing in Sri Lanka or Thailand, however, where that tradition is still strong. I don't see why you should search out places where the traditions are not accepted. Staunch monks are doing that in the hills of Sri Lanka, where they share the forest with wild elephants and other dangers. You could just get ordained by anyone, and then go your way. There are well-known Western monks who did not undergo a 5-year-nissaya. For the visa-situation in Sri Lanka you need some strong support, meaning good connections (places like Na Uyana are a good connection, but it can also be done thru other links to the Government).