The 1099 and stock cash-out tax issues make sense, and you are not hiding them. One is easily an oversight, and since they are a few years apart maybe they’ll both be a simple error. I bet you look real close at paperwork at tax time now!
Shame about the misdemeanor not being suppressed by the court system, but at least it’s only a misdemeanor.
I’m not a background investigator but I do have a past that makes you look like Mother Theresa. At one time I was severely embarrassed about all my errors but I have learned to dance with the skeletons in my closet. made mistakes, learned lessons, don’t repeat them (important), and let time work in your favor. From where I sit the misdemeanor is the only flag but five years of being a nice guy is good to have. Ten years is better but you have to wait for that, hehe. In my first background check I had expected them to come back and deport me. Honesty and candor go a long way in showing your true colors. Sounds to me like you’ll be fine. Please report back with the results for all of us!