Alright. I propose two nomadic routes if you are an American. There is the obvious SoCal to Washington route so I will not mention it.

We have Hawaii to Alaska, your working season will be in Alaska as long as you can tolerate the weather, you then boat or fly back to Hawaii while you work on one of the islands and wait for the next season towards Alaska.

Then we have South Florida to Kentucky to Upper Peninsula. This is a four season route, 2-4 months in each area depending on weather and work prospects. This is much more do-able, much easier, but less "hardcore" than the other nomadic option.

Of course there's endless routes assuming you don't care about weather, these two routes allow for conditions tolerable enough that you could simply camp or sleep in a vehicle and save money on rent.