11 years you want a blue water cruising live aboard, initial thought was catamaran but budget eliminates that, so you thought build it, but that is expensive as well, so now smaller fixer upper monohull.
Do I have that right so far?
You want to live aboard now, you probably want to learn or practice sailing meantime, you want your money to stretch so that you have the most seaworthy live aboard possible in 11 years......
From what I understand, (no personal experience just what I have read on the internet) after a year of covid it is a sellers market on cruising boats, everyone cooped up has watched youtube cruisers all year dreaming it was them and bought up whatever they could because they were sick of being stuck inside during the pandemic.....
This means whatever you buy now will be overpriced (maybe).
How about this..... Find the smallest floating hunk of junk you can practically live in for the next 5-10 years. Have it surveyed, you need an 'ok' engine and 'ok' rigging and sails. They don't need to cross oceans, but they do need to get you a couple years of playing around. Then spend the next few years 'fixing' it up cosmetically, refurbishing all the wiring, plumbing, interior, exterior, etc..... find the cheapest place you can tie it up during that time with the least amenities (none if possible) and live as spartan a lifestyle as possible. Then in 10 years sell it for what you bought it for and buy something like this(randomly picked off the internet)
https://www.catamarans.com/used-sail-ca ... eno/799955
Spend a year getting used to it and making it bluewater ready and then head out.
I think that is the direction your mind is going... not sure what is the best approach really, like everything there are lots of compromises that have to be made for your specific wants and needs.
Best way to get the most boat after X years is to drastically downsize lifestyle (rent, utilities, entertainment, eating out, electronics, toys, etc....) and work 50% more every week.
Can that be done on a boat? maybe... I don't know. The romanticized dream is there for sure, but what is the real cost of living in a run down boat under the bridge? Repairs and upkeep, heat and other expenses will catch up to you quickly.
The other thing to consider for planning, once you have your perfect blue water boat and head out full time live aboard, the spending doesnt stop. You still have all of your utilities and groceries and living expenses, they are just different. I think carefully done, once you have purchased and upgraded your boat you can live aboard as cheaply as you can on land, but I don't think significantly cheaper and you pay the price of downsizing your lifestyle significantly.
A lot of those choices and compromises will depend on your significant other (and if you don't have one, then the chances of finding one). You could rent a trapping cabin 50 miles back in the hills off the grid and road system cheaply, cut your own firewood, grow a garden, hunt and raise a few meat animals, and you would still end up having to buy supplies, clothes, ammo, medical, etc.....
Enough rambling from me sorry. I am in the same boat as you, looking roughly 8-10yrs out, wife and I are both committed to the dream, and working out the best way to realistically achieve it. Fortunately I love to build, and so it is easier for me to shift those compromises in that direction. Wife likes level floors, and doesn't want to 'live in a cave' so it will be a multihull. Meanwhile we are both working two+ jobs and saving every penny we can