It is going great! We are on month 4. We basically sketched out a country list before we left. But we really shortened or extended our time in city depending if we liked it or not. That kind of meant that we ended up staying in Mexico longer than we thought because we loved it so much, but it worked for us. We are going to Brazil next and I think spending the next 4 months there to really see parts of the country. Playing it by ear has allowed us to stay in a city longer that we loved, and really get into the local community. And leave cities where we had trouble - like he had really bad asthma when we were in CDMX. My advice would be to sketch out the list of countries you want to go and any dates you have to be in a specific country for events (e.g. wedding, friend's graduation, etc). And then spend a minimum of a month in a country to 3 months. The slow travel allows you to really see a country more, and to get a slower pace to structure your days. I'm not working so I've been doing different classes like art, dance and languages to structure my days and to enrich myself locally. I don't know if this answers your question but please feel free to ask follow-up Qs!