Upvote:2
With your three months on, one month off pattern I'm not surprised you've been denied. That's exactly the pattern that looks like you're trying to live in the US. For that reason alone you're unlikely to get a visa right now, and if you do get a visa at some point and try the same thing again you're likely to be denied again.
For a new application:
For your 'criminal' record: answer the questions you're asked honestly, but don't volunteer anything else. You're likely to be asked about convictions and pending court action. Don't mention anything where no action resulted unless they specifically ask you. A DUI sixteen years ago is unlikely to be an issue.
Good luck!
Upvote:3
At this stage of your immigration history things become too complicated for strangers on the Internet to deal with. What you need to do is hire a US immigration lawyer, who will advise you further on how to proceed with your delicate situation. We likewise cannot predict the odds of you receiving a new B1/B2 visa on time for your November visit and this is also where an immigration lawyer would be in a better position to advise.
Submitting a shaky visa application now would be much worse than not submitting one at all. Take things slowly and don't apply for a visa until you're confident your odds are good.