That looks great! Very cozy.
The first two weeks, almost every morning, yes, completely questioning my sanity and thinking about what I gave up as every little hardship arose. Things like where we put specific items (until you get a system down where every item "lives" and have everything labeled, it's a nightmare) and figuring out where to sleep while it's getting dark, and wondering if what we estimated we'd spend would hold true...so yes, lots of questioning!
But after week 3 or so, we started really hitting our stride. Getting a system down for stuff like when to change campsites, how to be patient with each other's quirks, thinking in terms of opportunity instead of hardships, all that.
Very excited for you!
You end up protocols and rhythm it sounds like. Nice to problem solve for yourself instead of your boss eh? Dad travels alone. A small space with 2 people would def. be a challenge. Especially during bad weather (trapped inside).