I'd go back to school to learn how to do and get the certification for my dream job. I'd start a small business on the side, serving an underserved niche and not really needing to be profitable - even working there on days where I'm in town and not hauling cargo. I'd invest some of it, so that the money could help grow itself. I'd get my transition done and over with. I'd buy some land - one lot to live on, and all adjacent lots as a buffer zone - and I'd build a modest house on the one lot I'd be living on. I'd give whatever I could spare to charities and activist causes I believe in.
And I'd still drive one of two old and beaten up cars, but I'd also buy a flatbed wrecker. Just because I could.