The plan you outline is certainly doable. It is even possibly doable with your current budget plans. However, it is only doable by a small percentage of experienced boaters.
I am not going to discourage you from your dream. I do recommend that you have a back up plan or at the very least a sizable cash reserve to weather the unexpected which will pop up on such an adventure.
Note, you can not stay year round in Canada with out the proper Visa’s and you won’t find any suitable winter anchorage in the US until you reach the Sacramento delta.
Yes sir, I under stand that, Canada summers, and down to the SF Bay Area to winter first seasons. And yes on the money, will have a good stock pile in reserve, which is why the 50k budget, to ensure I have plenty of reserve for unexpected expense.
I have made a moderate wage my entire life, always able to supplement my income by either second job, small home business, like here in colorado, summer I grow a large garden and attend farmers market on weekends, winter I plow with my quad. Currently selling off a lifetime of collectibles, sports cards, coins, paper money, beef up my reserve.
I’m not devoid of hardship in my life either, been here in colorado for 27 years at 7k ft, many years I’ve had to melt snow to be able to flush the toilet or make a pot of coffee. I can take it when times are rough. Doesn’t bother me.
I’m not going to be the boater, chilling on the rear deck sucking down sundowners, that is not my style, i dont drink or use anything that will mess with me, I will be fishing, foraging, pulling traps, or putzing around the boat or just enjoying the area with all the toys available to enjoy the water.
We have a two person ocean kayak, snorkeling gear, spear fishing rigs( lakes here in CO) 12 ft Hobie holder sailboat, and with a dingy and recent purchases for the boat aka underwater scooter, drone, gimbeled video camera, and computer equipment I feel like I can make enough vlogging, shooting are escapades on YouTube and such to pay for fuel and maybe more. My son is a graphics designer, past 15 yrs, and has a very good understanding of all that. We will be working as well and cruising.
I have spent the better part of two yrs now getting my ducks in a row