Jump in and worry about the landing later.
Of course there are headaches. Move past them.
You are on this forum and already cook for large parties. That doesn't guarantee anything, but it's a great start.
It's hard to foretell how your experience with the legal stuff will be. Reach out to you Heath department. Google "starting a food business in Indiana"
Just remember, no matter how much bs you have to deal with, you would have more if you were starting up in Southern California or Minnesota.
2 - WSM 18.5, 1 - WSM 22.5, and 1 - ECB Smoke n Pit.