Hey Joe G, sorry about the run of bad luck! One time I was in Lone Pine, and started down the street, and got a seat belt ticket! (I always wear it, only I put it on soon after starting down the road.)
Keep trying, you WILL get a Whitney Permit. There is another quick grab of permits at 7 AM on May 1. You have to be fast, though, as they all come available right at 7 AM. It will be all the lottery-won slots that were not paid for.
Also, there is a long thread here about the no-walk-ins. They will be online, instead. We have yet to see how well that works, as they are supposed to put the no-shows online as well.
You picked the wrong month to try to drive up the road. They are blasting rockfall off the road right now, but it will likely be open by May 1.
And forget the late Oct trip. It's cold, likely will be snowy on the trail, and the days are short. If you keep watch online, you can get an earlier permit -- especially in the one to two weeks before you want to go.