I think this project is feasible with a little organization beforehand and according to the chosen destination!
These are the points I would make before leaving:

1. Choose your destination, establish a route and prospect on volunteering, local associations, woofing, NGOs.
This allows to consider places for the stages of the trip that are more established. That is to say on a few days or weeks, one is registered in a local action with a framework or a structure of reception. Indeed, for services rendered voluntarily, one can be housed and fed. Thus it allows to discover the local culture and to meet the local populations.

2.  For places of "passage" to think of couchsurfing, in order to be able  to find accommodations and receptions safe and benevolent. Maybe also go to groups in social networks to find "good plans".

3. Learn about networks such as greeters to meet locals and create links locally. This is an initiative where meetings and visits are completely free and will always be free.

4. Communicate!
An essential aspect in a trip like this is the network!
I think it is very important to talk to his family and his entourage about such a project. And then, with a butterfly effect, friends of friends, certainly have contacts towards your choice of destination.

These are, it seems to me, basic points to develop this type of trip. However I also invite you to read, because a good number of travelers have already realized this type of adventure.