My move to WordPress.org looked nothing like this, but you have to agree these young college students look pretty organized.
Fortunately, for me at least, I chose one of WordPress's recommended hosts, Bluehost, who gave me the best of their tech support and direction. I also was lucky enough to come across the site, WP Beginner, which provides easily accessible information for those new to WordPress or those making the move from WordPress.com to WordPress.org.
WP Beginner offers a free transfer of your site from here to there, and again I received amazing tech support and education on what was happening.
Although there was a little reorganization and cleanup afterwards, I don't think I would have wanted to do it on my own or without these two amazing sites and their tech people.
I strongly recommend anyone thinking of moving their blog to do as much reading and vetting of the issues as possible before hand. It makes the waiting time while the truck is loading up all your blog posts and pages and moving them from here to there easier to bear.