You mention two words that I'll pick on: regrets and fear. You're too young to have regrets.
So, you missed some time with your girl(s). She/they'll get over it and most likely already have.
Fear: Sure, it's healthy, especially in sailing, since it prompts that most important aspect: thorough preparation. But until you've cruised locally before setting out on your dream trip, you will have NO idea what to expect, unless you've done some already, which I may have missed.
Many, many folks on this forum are a lot more accomplished than I am in
long term cruising, and are "out there." Others, like a64, are in the planning or early doing stages. But all of them have valid inputs for you.
I just finished a six week "cruise" from
San Francisco to
British Columbia in our 30 year old
boat, with my 28 year old son. I thought of it as a
cruise /
delivery (because of pending weather), he thought of it as a restaurant tour of northern
California,
Oregon and
Washington. We visited four
anchorages and a dozen
ports. Where do you think the
food bills were less?
And of the harbors/ports, most were incredibly inexpensive compared to what we were used to in
San Francisco for the past 35 years. Neah Bay was $21, Lapush was $15!!!! OK, plus $4 per day for
power.
You say you've read a lot of the earlier posts on cruising costs. All of the issues raised here have been discussed so many, many times already: It all depends on what YOU want to spend and what your lifestyle is. We can't change your habits or behavior, only YOU and your
family can do that.
And where you go and how much you choose to
anchor out WILL affect how much you spend. I don't care where you go, except perhaps in those local places, eating out always costs more than eating in. If it didn't there wouldn't be any restaurants left, they'd all be outta business.
The rest of your "equation" is the
boat and
maintenance costs. Again, these have been covered extensively in those earlier posts which you said you read.
You are in a pretty healthy position. You're young, you have $$ and you have a built in fallback.
I think you're over analyzing this. 3% or 4% won't make a hill of beans difference if you spend less and tuck away some for
repairs. What's so hard?
I'm 70, have owned boats for 35+ years, cruised extensively in Northern
California, owned this boat for 18 years - she's thoroughly "shaken down." And I just fulfilled my sailing dream with this recent trip: I crossed the
Columbia River bar, entered Lapush, and moored in front of the Empress
Hotel in Victoria Harbor
on my own 30 year old boat. We only "sailed" the last day, the rest was motoring north, but we had fun.
Go for it. KISS.