Hi Jackson
It's an interesting idea if you can work it. Most inspectors (at least in my area) will allow living in a wheeled structure only for a time before a full house is required. You can say you are in the stages of building etc to keep them off your back for a while but in the end they will want a house, unless you can get a hold of someone who is up to speed on the small house movement and will consider it. It'll take some work.
Now if you can get a hold of some acreage where you can tuck this building out of the way and blend it in so nothing stands out, who says you have to let the inspectors know at all.
There are some interesting stuff on youtube where people take enclosed cargo trailers and revamp them into campers. Might be easier to modify but you won't be able to make those small adjustments that makes the place yours.
Keep an eye on
http://www.tinyhouseblog.com and
http://www.thetinylife.com they usually give good ideas on house designs and sometimes how to work with codes in your area.