Couple more;
(Borrowed from your earlier post)
Then we sat down recently and realized how incredibly happy we were when we were living out of canvas WWI backpacks eating grape nuts and Spaghetti O's while enjoying just being together with no interruption. That was 16 years ago and we are like many others disillusioned in the current crisis in the world and we came to a simple conclusion. We both much rather enjoy life again then work so hard just to be slaves to things we really never needed in the first place.
Don't ever let anyone or any magazine pry that vision from you. Much of the culture, even the sailing culture is about the amassing of materiel (waterline length, extra gear, etc.) I gotta stop now, or else I may get on a rant again...
like this.My wife and I are noobs in the noobiest way. We have been on boats but know nothing about running our own boat. We have a limited budget for first boat purchase & year one expenses.
So our plan is to buy our boat and get certified on our particualr vessel to reduce costs since we are certain that it would be no problem (I'm sure some differ, I've been told as much) to learn as we go & best to learn on what we are going to actually be investing our future in though I will be taking a basic 101 on Lake Michigan in a few weeks.
Not sure what certification you are seeking (unless the reference to '101' is the ASA course). Courses are an excellent was to begin, is Lake Michigan your current home water? Your intro post said you had moved to Seattle, but I am not clear if that is where you are currently located.
What we have to spend for boat and running costs for 1 year $20-$26K
I'd rather do it for less but that's what we have.
Taking into account that I have already learned enough to know what type and aproximate size which is how I came across this site. Researching SB/LA cruising.
With caution you should be able to do that. One advantage of the current economic situation is that there are good deals available.. you just have to hold out for them.
What I think I know-:
1. Shoal keel/Shallow draft as we will be mostly taking this first boat only on the Pacific coast/Bahamas/Caribbean/Mexico and potentialy the ICW if we were to move from West to East coast (but East Coast is not likely as that is not where our dream lies)
Wise.
2. Boat must have a head (wife's single requirement) I'd be willing to do bucket style for extra storage but she isn't.
You will avoid hastles with local authorities with some kind of approved MSD. I am looking at the Natures way composting head myself. I love the idea of getting rid of the black water storage tank (and it's space) and exchanging it for something I will use.
3. I can easily expect 10% of boats value for yearly maintanence (that's right?)
If the boat is in good shape when you depart. It is a fine balance between what to fix before you leave and what to live with. Lots of opionions available when you are considering specifics.
4. looking at 25'-30' to accomodate these needs but not looking at larger and likely to do it on a 25'-27' for budget purposes.
Sounds like a good range.

This is my first plan in very basic form so please tell me it's possible on the above budget (of course it's subject to our ability to cut costs where possible and that my wife is employable almost anywhere in the world.)
My first Plan:
Write a plan/Start a log/Come up with 1 years running costs
Good to have a portable skill. Does the massage therapy license carry reciprocity in your intended (US) ports?
Lessons/Coast Guard Certification-Live Aboard first so I can get cert on my own boat and rigging?
The ASA / US Sailing courses are good (with the right instructor). Don't go too far with them (on your budget). Consider the free / cheap courses available through your local USCG Aux / Power squadron.
Survey the boat/Hopefully meet someone to help us understand outfitting for our needs
The survey can be a great investment, or a complete waste of money (especially on a non-financed vessel). You will know your comfort level, but make sure if you use a surveyor you fond a good one.
....Mooring-1 year paid upfront at some marina somewhere (or substitute this with anchoring where possible to keep cost down?)
If you can, avoid marinas. They will really suck the budget down. Anchoring makes it tougher to work on the boat, as well as the risk of theft / damage. It is not an easy decision, but I would work this one.... research the local options. You will probably find that there is quite a range in the price.
Emergency Equipment-minimum CG requirements
Given.
Communication Equipment-minimum CG requirements/Radio operators license;Laptop and required inverter;Software
No CG requirement. Avoid buying anything beyond a simple VHF (you can get by with a handheld to start with, and it will be a good back up if you upgrade later).
Navigation Equipment-
Avoid buying expensive chartplotters. Get a handheld GPS, and learn to use a chart. This technology will not fail like your laptop WILL fail as soon as you rely on it. GPS's are a dime a dozen used... don't increase the budge for a boat that has equipment installed.. it is likely already outdated. Bottom line, save your money here. If you start with a chart (and hand held GPS) you can always get a chart plotter later. If you learn on a laptop / chartplotter you will have a TOUGH time learning to navigate without it when it fails 'out there'.
Repairs Equipment-
You will likely get this kit together as you get the boat ready. You can never have everything, and you will likely take too much and yet still not have something you need.... it is part of the adventure!

Avoid complex systems and you will cut down the spares and repairs.
Galley-Fridge/freezer(LARGE icebox)
Some here plan to / do without. My First Mate requested it... I was glad. Keep the size as small as you can, they ALL suck amp hours.. even the good ones.
Dive Equipment-(less important but something I want to learn as part of maintanence ie:hull cleaning/prop repair without drydock)
Lots of discussion here. I have it aboard Faith, but a mask and snorkle are pretty much all you really need for most maintenance tasks.
Overall provisioning-(How long can we stay self sufficient with size and fully provisioned)
Lots of good discussion on this here. Again, you will likely take too much... yet still forget things. Nice thing is that where ever you go the people eat THERE too.

Places for Adina to work or what she can do- Massage/Spa Manager
Places for Greg to work- Maintanence/Repair and overall running of onboard duties
I would look into the license reciprocity issue, but your stops for work are likely to be dictated by unforeseen circumstances (major repair bill, or just liking an area and wanting to stay longer) tough to predict.
What I need to learn:
How to (sail/navigate/maintanence/repair)
Diesel Mechanics or engine repair
Electrical systems and repair
Knot Making
Laws for the areas we will cruise (Taxes ie:local and U.S. income Tax while working outside of U.S.)
Never ends. Courses are good. Free courses are better. Check with your USCG Auxiliary, they offer a good boating safety course and IIRC only charge for the book. The Power squadrons are good to (especially their navigation course).
Good luck, look forward to following your progress!
(man, that was a long post).