Jared,
I have lived aboard for the past 33 years between SB and Ventura, including 7 years on the hook in SB. You are right about the slip situation is SB. The waiting list hasn't existed for 20 years, it is now more of a free market and a 30' slip will cost you about $60k. As Paul said though, that would be your best option if you can swing it. There is only 1 person on the
liveaboard waiting list right now.
Of your options, I would guess that option 1 is the most workable. I would focus on Ventura since Oxnard would add another 15 min to your commute and Ventura has a more favorable tack to the Channel Islands. As far as I know, 30'
liveaboard slips can still be had in Ventura. A quick call to Ventura West Marina (which allows 50% liveaboards on some docks), Ventura Isle and Ventura Harbor Village will tell.
Option 2 is going to cost you. About the only affordable place between Ventura and SB is Carpentaria. My girlfriend pays $950 for a 18'x18' cottage there with her daughter living in a tent on the
deck. Typical 1 bedroom apartments are around $1300 to $1500/mo. But you are right about the space and it
is doable.
But you knew all that which brings us to option 3. It can work and I will probably do it again in the near future as I can't afford a slip for the
new boat, but there are some difficulties.
1. You need a very tough and understanding girlfriend as she will have to get up early and make her way to the harbor in the dark to get to work in the morning, learn to love scraping dinner off the floor and put up with some sketchy neighbors. It can be very cold in the
winter if you don't have some way of
heating the
cabin and a hot
shower is 2 miles upwind.
2. The
winter anchorage has been moved from 1/2 mile east of the pier to 1 mile east of the pier from November to April. There is much less protection out there and the anchorage is pretty rolly much of the time.
3. Slips are usually available when
weather comes through but your really have to keep a close eye on it and be ready to move at short notice. This can be tough if you are working a 9-5.
4. As housing and slip prices soar and more people become homeless the number of derelict and unattended boats has risen in the anchorage. These can be a real hazard when the
wind comes up and they make their way to the beach. It is best to
anchor outside of everybody where there is even less protection from the waves and swell.
5. As an anchored out liveaboard you will be viewed by the city officials as an annoyance that they would be glad to be rid of. If your mansion burns in a brushfire the city coffers will open wide and Jackson Browne will do a benefit concert for you at the Bowl. If your boat goes on the beach you will be cited for littering and given till sundown to have a bulldozer chop it up and get it into a landfill.
But aside from that, the sunsets are spectacular, the phosphorescence is amazing and you have the best view in SB.
Good luck with your decision and I would be happy to answer any questions
Mike