Instead of tiny homes, try thinking within the regulatory box of "classifies as an RV or towed camper". That might allow you to bypass some of the other limitations you were facing.
They still seemed poorly laid out with crummy bathrooms (in this case, no piped water and a terlet that was basically an indoor plastic porta-potty) but I did admire the law-skirting.
There can also be avoidance of property taxes in some states I believe.
You're right though, I think the key to making this work without trying to get laws changed is finding the right combination of laws and solution/use case that remains within the regulations. This is definitely doable in certain locales and not in others. If I'm really going to make what I wanted to do work, I will have to find the right balance of factors.
I was so surprised when I started reading zoning rules for plots of land that I was looking at to build a tiny house - some had minimum home size requirements, others had explicitly outlawed the use of any such wheeled dwelling precisely to prevent people from doing what you said. Some of the larger plots of land that were quite inexpensive required a 2,000sqft and up dwelling to be built if they were purchased and used for residential purposes!
This means having it sitting on, rather than attached to, the ground, and having some "skids" on the piles.