Hello, and welcome!
Do you have any specific Oregon questions? How far are you in your planning? Portland or small town/rural? Kids, school, job questions?
Oregon is pretty great in 1,000 ways. I don't know about any more or less free life - I think any area is what you make it. I do feel Portland is pretty accepting of unusual lifestyles. Most of the rural areas are more conservative (not all!). I have met with little or no resistance to unschooling or tattoos (I have a fairly professional job these days, and a tattooed sleeve doesn't upset anyone).
A couple gems of Oregon life: great drinking water from the tap, no sales tax (so far!), and the attendant pumps your gas for you. The climate is a plus or minus, depending on your perspective. I love Portland's cool rainy weather. Other parts of the state have different climates. Eastern Oregon has distinct seasons, with HOT, dry summers and snowy winters. Southern Oregon, mountain areas or the coast, each has its own climate.
Portland is a major metro area, but feels like a small town in many ways. Skiing, the beach, rivers, and forest are all nearby. The city is pretty bicycle friendly, and has good public transportation. Each neighborhood has its own flavor, and anyone should be able to find where they "fit".
Sorry I didn't see your post sooner - come back with specific answers and I will give it a try!