I've really studied this project, top to bottom. I've talked to the city about 10 times, and have quotes from building companies, and moving companies.
I've decided not to move forward with the project - for two primary reasons:
1. I just can't get my head around throwing away a perfectly good 2 car garage. I see guys on here making the most of doubles and even singles, so why am I trashing a perfectly good double? The best I can get out of it is $2500, and even that is hit and miss (I had about 5 bites)
2. The new build is $35k before I even consider furnishing it. That number just seems really high. I don't have that kind of money to throw away. I'd far sooner use that on things like buying quads for my son and I, or putting money into the boat or car.
On top of all this, as I'm sure you all have experienced, my wife hated the whole project. She pretended to be on board because it made me happy, but she detested every aspect of it. I knew I was in for a year of torture spending all my time building a structure she couldn't stand.
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The good news in all this is after we had a good dialogue, she said more about what she wanted for our backyard. It exposed some ideas I never had before.
Firstly, she wants more sun. Right now we have a covered deck, and 3 large trees. She wants the cover on the deck gone, and the trees gone. I'm a prairie boy and cutting down trees is heresy to me, however if that's what it takes for her to enjoy the yard, then so be it.
Secondly, with the trees removed, I now have options I didn't have before - specifically making the garage longer instead of wider. This way I can maximize the "parking space" for parking and automotive repairs. The new added space can then become my dedicated workshop.
I've actually discovered this winter that by being clever you can get a lot out of less space. Right now I have my whole boat in there, all my tools, and I still have room to work on a full-sized truck. If I get all the tools and storage racks out of the way, I could even place a 4 post lift inside!
Thirdly, and I have to give credit to Ainsey for this - I can raise the entire garage up to make more height. It should be a relatively easy project compared to what I was looking at before.
Lastly, I'll go forward on the Boat-Port idea. I like having the versatility of an outdoor space, as then I can do my wash-downs there, and have lots of room to park other things without the restrictions of a garage door. For instance, today I have a car hauler there. The added height on the garage also makes the roof lines work far better for this.
Green is the garage expansion to the west, while the blue shows the boat port to the north.
So that is the plan as of today. I'll be doing detailed drawings in the next few weeks. The best part of all of this is that I don't need to rush. If it takes 3 years, so be it. The cash is literally in the bank so I can take my time and get it done, and still enjoy my toys during the process.
I'll probably start a new thread for this new build.... apologies to anyone who reads this 4 years from now and discovers no ending

One day I'll build a true dream garage, but not on this property.
Thanks for all the contributions. I hope you all follow me to the new thread! I'll post it here when I get to that stage.