In my experience, ridding the decades of clutter and dealing with the shore-based life was no fun.
But living aboard was frankly much easier than anticipated and I sometimes have difficulties understanding those that say it is a tough life. We CCd throughout the year and had no real difficulties with fuel, supplies, electricity generation water or any of that at any time It lead me to think that the grumblers had a much easier life than me, prior to living aboard.
It must depend on your circumstances up to a point; we had many years experience of holiday boating, so there were no fundamental surprises (apart from the ease). On the other hand, I worked although did not need to go to a place of employment regularly. Also in reasonably good health.
I wonder whether being a frequent mover OR a having a permanent mooring is rather simpler that a hybrid arrangement where you need to keep the car or stay in close proximity to somewhere; I would not have enjoyed the faff of shifting a car around or trudging along a dark muddy towpath to a cold boat after a day at work. But even when shut-in by unannounced stoppages or truly inclement weather, you soon adjust and the time passes joyfully.