My visa got cut short, and I kept my original plans which ended over a week after the grace period. I then reapplied for a visa, was granted one, and visited another few times. My visa is no longer valid and I would like to travel on an ESTA. Will I have any problems?
You can certainly try applying for an ESTA, making sure to answer all of the questions truthfully.
If your ESTA is approved, then you are free to travel to the US. If your ESTA is refused then you will need to apply for a visa.
As is always the case, having an approved ESTA (or even Visa) is not a guarantee that you will be allowed enter the country, but almost certainly you will have no problems presuming you answered the questions in the ESTA application truthfully.