I am sure that WnW's blog will be a big help.
We have found that the biggest obstacle to success in the Living aboard and/or Cruising life is the inability to part with stuff. This one is second only to suffering withdrawals from facebook, email, telephones and all the other trappings of modern life, while away from the dock.
Living aboard at the dock is fairly easy unless one has physical disabilities that limit one's ability to get from dock to boat. You can have a storage locker (Or use your car or van for storage) for all the stuff that doesn't fit on the boat and you can keep your car and cell phones, 9-to-5 routine, cable TV etc. It is just like living in a floating trailer park.
Cruising, i.e. actually leaving the marina with no specific plan to return, is either much simpler or MUCH more complicated. Your choice.
Want to know what it is really like "Out there"? Maybe THIS
will help give you some idea.
Laura and I have been living aboard together for over fifteen years now. We have been actively cruising, full time, since May 2007.
Before we married in 1999 she confided that she was apprehensive about crossing oceans and being at sea for weeks at a time. I arranged for us to spend our honeymoon sailing as crew from Vancouver, to Kailua-Kona on a sail training ship, the Endeavour Replica, a 97' LOD three masted wooden square rigger. That three week voyage, as they say, "Sealed the Deal". After that, we immediately made plans to quit our jobs and go cruising.