Everyone is different, so these are my personal opinions of what I would do if it were me:
1) 800 sqft living space isn't all that big, at least, for someone who has the funds for two trucks and a boat. I would make it at least 1000-1200 sqft; after all, you're a grown up right?
2) I assume you plan on having a lady friend or two over at some point in time; they won't care about the shop, they'll care about the living space. I highly suggest you spend some money in some nice stuff for your living space. If it's all about the shop, you'll turn many girls away and give off the wrong type of vibe of who you really are.
3) Walking through the kitchen to your bedroom isn't very "nice". Eliminate the 6 person dining table, and put the kitchen in the corner facing the living room. Open concept with easy access to food and a bar top is excellent when having your friends over. The game, the shop, whatever, it's nice.
4) In the current kitchen area (now moved), put a nice oversized counter height 4 person table. Really, it's just nice for yourself or two people (lady friend) but you can have more people eat there (friends) or a place to put food when your friends are over.
5) Make the master bedroom bigger. 15x15 at least (my current is 20x20, a little obnoxious at first, but you'd be surprised how you happily get used to it). Have at least a king size bed in there, plenty of nice furniture, etc. Remember, the ladies.
6) LIGHTING is what makes or breaks a place. Definitely install some nice modern fixtures and lots of recessed (and LED) lighting. It'll really make a place pop, and they're about the same price as traditional fixtures nowadays.
7) SPEND MONEY on nice things in the kitchen, that means stainless and granite or some other high end top (there's plenty of great deals out there on this stuff now). Don't put a cheap laminate top on there, it'll completely cheapen the feel of your entire building.
8) Add more windows, and bigger ones. Especially the living space, but I'd also consider more windows in the shop. If you want to really be nice, make an entire wall nearly all windows. You'd be surprised how awesome natural light is. Even when it's raining, humans naturally prefer to be outside enjoying nature (while at a nice and cozy and dry 72 degrees, of course).
9) Don't forget your outside parking area (with perhaps a nice deck or something to sit outside). You'll need to park SOMETHING outside at some point, whether you're just running in the house for something, or you need some open shop space for a weekend project, or you have a few friends come over.
Since you are starting from scratch, most of this stuff you can do for a great price. Normally when doing stuff like this for a remodel it gets expensive, but it's possible for great deals when done from the very beginning.
In the end, there's nothing like an awesomely sized shop that's a part of a really nice living space. If your living space is "just" a living space, well then it really makes your entire place feel lower end. You just have a large "cheap" building with an obnoxious shop and some cheap living space. You're already going all out for what you want, so go ahead and do it right - have a beautiful, modern, "expensive and custom" place with an awesome place for grown up toys
