Katya - You lived in Muskoka? My baby sister lives there, I'm further north but even driving through gets me jealous and wanting to move there. I'm in northern Ontario and it sure is gorgeous. There is just something magical and tranquil about the Muskoka region. I bet you miss it!
Jody, I think it makes sense both ways, depending on your options. IF you have a reliable person with land that would let you live expense free on a section of their land, for a period of time, I would say do the tiny house first. The thought being, if you get the money in the next couple of years to finance the tiny house, you can skip the add ons (porch, big garden etc) and live simply and pretty near to free, on a friend/family members land for maybe a year or two. You could then bank even more savings, so that after a year or two, you could buy land for cash. If you don't have a reliable place to land with a tiny house first to make it practical to do this all over time, in cash without loans, then I'd do as suggested by others, and get the land first. Part of tiny house living is the desire to cut cost of living, often to allow less needed ongoing income, meaning life need not focus on such a rat race for profitable income. More simple living based on more than career etc. Hope that is making sense. I would focus on doing whichever of the two steps will be best as first plan of action, the goal being the most sensible way to ensure the soonest date to make these things happen without burden of debt etc.
Im excited for you. Can I be your first guest? I'll bring a tiny house warming present lol.