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I've done a lot of this.
One thing to remember is that the things you look back on fondly will be the most frustrating and painful in the moment. Try to keep that in mind when things go sideways. Nobody remembers the times when everything went perfectly.
That said, my fiancee and I have developed a set of travel ideals to keep us both from feeling like hobos.
Two nights, minimum. We try not to spend single nights anywhere. It isn't worth it. We don't end up with enough time to see anything. The big exception can be first and last-day hotels.
Four nights after three shorter stops. We need the extra day to crash and/or do laundry, etc.
Try to spend (at least) a full week somewhere. We both really enjoy the simple process of learning to live somewhere. Learning the transportation system, buying groceries, etc.
No Airbnb for less than a week. The hassle and uncertainty of getting situated isn't worth the trouble.
Depending on distance and timing, it can be worth it to double-book the last night at an airport hotel. The last mad rush to get checked out of an apartment, and get to the airport on time isn't ever fun, especially somewhere like CDG in Paris. It can be really nice to just remove that stress from the equation.
I hope you have a fantastic trip!