I'm retired from the Marines at 100% from only ten years of service. I was injured in Somalia and Iraq, so I can't play GI Joe anymore...
That provides my liveaboard kitty and keeps a house together for my wife when I'm out on the water.
Now, ok, so living on a sailboat in Colorado or travelling to Mccauneghey (sp?) in Nebraska with a whopping 100 miles of shoreline isn't too big of an adventure, but I have learned how to provision, anchor
in storms, run for cover like hell, sail with bare poles, heave to in whopper squalls, change sails ten times a day to suit our crazy weather, and much more, all the while encircled with beaches to run aground on. I guess that is an adventure in itself.
As far as my boating lifestyle goes, we have nothing but fun. When my boat gets wet, I stay with her for weeks at a time. There is time to work on the boat, and time to have a drink, or time to fish. We also sail for hours and hours... hahaha, I've even sailed for 19 hours around the lake just to see if I could handle singlehanding when we go to the gulf.
I guess I'm saying there is a lot of time to moderate all the days' things to do. It would be like having your boat 25 miles away and trying to drive to it each day to work on it, or being far easier to just live on it and work, where you can spend more quality time with her.
Living aboard is more productive to my boat than parking her in the yard and working on her when I "have time".
I don't think a good cruise would be a "two week vacation" from work. I recently met a guy who chartered in the keys, and in order to meet his plans to visit each port, he short-handed his ship with wife and kids to get everywhere as soon as possible. They were flying a 150 genoa at night with the motor pushing along too so they could stick it at hull speed all of the time to make the ports. The third night, he had an evening squall in the dark and the boat rounded up into the wind, the jib
backed, and knocked the boat over into the water on the other tack, leaving them with a ditch bag and dinghy
for a few hours until they were picked up. I understand that he left the companionway open and the boat downflooded and sunk in minutes.
That gives me the impression that if you're gonna cruise, don't set a plan with a "must-get-there" attitude, it could end up hurting your family or self because you'll be rushing. Rather, just save and sail at your own pace and be safe with a leave of absence from your job, or quit alltogether!
I hope that stuck to your topic a bit...