We stayed in our small starter home while our peers upgraded and upsized their homes several times. We then downsized (sold) our house and upsized our boat.
We certainly could not have done both, so we made a choice.
And both of us can sail, dock and anchor this 40' catamaran single handed no problem - in fact, it is almost always how those things get done anyhow because they are so easy the other person isn't required.
Mark