One thing I notice in these posts is folks really aren't coming clean about where they are at; Are most liveaboards really well-heeled suburbanites slumming? If so guys like me would really like to know. I chose the lifestyle for many reasons, not least of which is I want to live free and thet means inexpensively; as someone observed, the more dough involved in anything, the less freedom accompanies it UNLESS YOU GOTS LOTS OF DOUGH.
I am a self-employed urbanite who paid off his house in eight years by never taking a vacation, using the same 1992 TV with rabbit ears and by not driving a car. I then used the house for a fresh $200,000 mortgage to pay for a 40 foot cruiser plus enough money to reno the house for two pairs of tenants, who will pay down the mortgage (and pay for our diesel) while we cruise. I'll work while I'm gone for a five-year (hopefully) circ; I'll sell the boat when I return (in Europe, because they live proven steel boats), and I'll never retire because I don't have a pension and the demographics will look pretty ugly by 2026, anyway....so I'm taking my retirement in my late 40s with my wife and kid while I can.
It's doable if you can exercise discipline and stick to your goals. Job 1 is simply not spending money on crap: we did five years of double mortgage payments while having a single pair of tenants in order to be in a position to use an appreciating shack in an up market to capture the increase. If the boat itself is paid for, that's half the battle, because boat loans are crazy.