I lived aboard for 10 years and started out with no sailing experience. In the beginning I used the boat as a motor boat and sailed with friends (crew) on fair-weather days. It's not the "right" way to get into sailing, but it worked for me.
My dock neighbor had a bayliner buccaneer sailboat of 28-ish length. I looked at that model also because it seemed to have quite a bit of space for the size and price was low. I'd say they'd be sutable for your needs, but on the other hand, if you really want a comfortable live-aboard and do not have ANY plans of taking it anywhere, a powerboat with dead engines is a great way to go. There are many good powerboats with gas engines that are either dead or dying that people are literally giving away.
The advantages of a power boat for living aboard are many. First, you have MUCH more space. Second, there is almost always standing head room. Third, the big windows help keep the dreary darkness out and make it feel bigger still. Fourth, and my favorite part, you can see out of your windows while sitting down in your living room. This helps keep the "submarine effect" from happening.
Now about the living on the hook thing. Living aboard at the dock is easy and fun. Like I said, I did it for 10 years and could have done it my whole life on a 30 footer if not for what my family wants. Living aboard on the hook is MUCH more difficult. Electricity will be a problem and all live-aboards at anchor around here use generators. You will be constantly lugging gas, water, food, trash etc in your dinghy. Heating your boat will be a problem. Whatever you heat with with (diesel, propane, wood) will have to be ferried back and fourth. In the fall and winter the wind and waves really pick up and your ride to work and back home will be wet wet wet and very cold.
Where are you planning to anchor anyway? Chuckanut bay has some perminant residents but you have to check out where you would be motoring your dinghy to and if you can park a car where you will be motoring to. Also, it'll get REALLY windy and rocky at anchor around here in the fall/winter.
At the dock you can use electric heat and the boat is toasty all the time. You can have WiFi, marina showers and laundry etc. Bringing a girl back home to the boat for a sundown drink (and hopefully more) is much easier if you're on the dock than if it involves a dinghy ride in the wind/rain as well...
Here are a few cheap power boats that would make awesome live-aboards. Some even have functioning engines. Check out the second one, it's always a good thing when the broker says "Owner says make it go away."
I bet you could pick that one up for 6K and it has functioning engines and looks good.
1964 Tolly Craft 27 Sedan Power Boat For Sale - www.yachtworld.com
1972 Trojan 30 Flybridge Express Power Boat For Sale - www.yachtworld.com