Well, the bottom line is that passenger info on any aircraft that enters USA airspace is recorded into CBP databases. If you have criminality then this is noted and automatically downloaded. CBP will see it and it is already in the system for example if you try crossing at a land border a few months later. Now the CBP officer may or may not do anything. You can be assured that the info is in the system but will depend on the officer if they act upon it or not.
The problem is that there is so much inconsistency at the borders..at least in B.C. since I cannot speak on other areas. Also #10 I really recommend people research to even see if they even need a waiver before they spend money on it. People can go to appropriate sources to see if they even need a waiver. I am not talking about a September Letter since there is a way to get cleared locally at certain borders if you do not need a waiver. People often call us and ask if they need one. Based on the circumstances, I sometimes tell them no and to have a nice day. We charge them less than a penny for this service and just ask them to send their friends to us in the future....and they do. If they need one and won't qualify for a September Letter, then we quote them our fee and they are free to either use or go somewhere cheaper. Understandably, I am hesitant to publish a list of offences that do not require a waiver or qualify for a September Letter since this is our area of specialty.
Do not ask a Discount Waiver Company because they will likely tell you yes so they can get the waiver business.
In your case #10, It seems like you would need one since I assume that you do not have USA citizen parents, are not First Nations and do not qualify for other areas of relief. I just hate for someone to apply for an unneeded waiver since those people can say the wrong thing and talk themselves into needing one. Not every offence requires a us entry waiver.