live on/learn on/cruise on
I don''t know much about the Bay area, but people do live there on their boats. If you are open to moving north, Puget Sound offers a lifetime worth of cruising grounds in every kind of condition. Usually the summers are warm and dry with winds 5-15 knots although this labor day weekend saw winds of 25 and some gusts to 40mph, so sometimes there is a good breeze. Cruising grounds go from Olympia in the south to Haines Alaska in the north. North of Puget Sound are the San Juan Islands (172). In Canada there is the Gulf Islands (over 700) and the cruising mecca of Desolation sound (about 100 miles north of Vancouver). The west side of Vancouver island is outstanding and gives many people their first taste of offshore sailing. Just so everyone doesn''t move here, it does rain in the winter, but the best sailing winds are then also, go figure. Foulweather gear and a heater make it fun.
The state has really tightened up restrictions on liveaboard spaces in Lake Union and the Ship Canal along with Salmon Bay, Union Bay and in Lake Washington (all basically in or near downtown Seattle). However, there are usually always Liveaboard slips available in Bremerton which is across the Sound, but has a ferry to downtown Seattle. Bremerton has the Navy shipyard as the major employer, but many people ride the ferry to Seattle every day for work. Tacoma and Olympia may have liveaboard spaces, but I am not familiar with those marinas in the south sound. Olympia is the state capital so government jobs are there and the capital and many government buildings are in walking distance of the marina. Tacoma again has marinas all around downtown.
Everett north of Seattle has liveabord slips and is the second largest marina on the west coast(After Marina Del Ray). If you buy a boat with Everett moorage, you are allowed to keep the slip, otherwise there is a one to 10 year wait for a slip depending on the size of the boat. Anacortes has many marinas, but I don''t know if any have liveaboard. Bellingham has a waiting list. Blaine is as far north as you can go in the US usually has slips and alows limited liveaboards. Friday Harbor has a big marina and some people live in it, but if you landed a job there you would be a lucky dog indeed. I would love to live there.
I have kept my boats in Lake Union and Salmon bay in Seattle and found that is great for day sailing in Lake Union or Lake Washington, but to get to the Sound you have to got through the locks which can be a pain especially on a busy weekend. I have also kept boats in Everett, Friday Harbor, Anacortes, and Blaine. The best exploring is from Anacortes or Friday Harbor, but the best sailing wind is from Blaine. In the sound the best wind is between Edmonds and Kingston(both have very long wait lists) and Shileshole to the south and Everett to the north. Slips run from about $4.25 per foot up to about $11 per foot. The closer to Seattle the more expensive it gets.
Anyways after the travelogue, I would recomend whereever you live to get the job and an apartment then get a cheap boat to learn on. I bought a 24 foot San Juan for $4000 as my first boat. It was very basic with just a compass and an outboard and 6 sails. I sailed the daylights out of that boat for 8 years and ran it aground a couple times. I have a friend who bought a 36 foot boat and was almost too afraid to take it out of its slip. I ran into another person in the same condition. Always wanted to sail, bought a big boat, and is afraid to back it out of its slip. I recomend getting a first boat you aren''t going to be afraid to trash. I think you will be a better sailor for it and a more confident one.