[Porsche-O-Phile]

1. I've been passively looking for a while. Catalina seems to make a good introductory-type sailboat that you can grow into. I'm sure some others with more experience here will chime in too. . .

2. Personally I'd say no smaller than 40', but opinions may vary. You could probably do it on a smaller boat if you were very careful and put a lot of thought & planning into it. People have before. . .

3. Yes and no. . . I'm actually looking at one since it's virtually impossible to get into traditional housing here in SoCal (either condo or house). If you do it correctly and the boat is properly equipped (stateroom & head, certain berthing & live-aboard requirements) you can actually qualify for a homeowner's tax deduction, which would go a long way to helping us save for a "traditional" home. Call me nuts, but it just might actually be a wise investment from that point of view - on top of being damn fun, a getaway and a non-depreciating asset (depending on the type/year/model you get).

I personally LOVE sailboats. I have a decent amount of experience from when I was younger, but it was all on much smaller one-and-two person single-mast craft.

You can get a "decent" 28' or 32' boat for $8k-$15k but the slip fees will be what kills you. I'm checking now but there are prohibitive wait lists at most of the marinas around here and the rates are highly variable. . . If you can work that obstacle out, perhaps by buying boat & slip rights combined, you could do pretty well.

I suspect to have more information in the next 4-6 months. If the housing market doesn't seriously start correcting in that time, I'll probably seriously pull the trigger on this as a "Plan B".