Hi all. Thanks for the ideas and thoughts.
I finally got around to measuring the driveway again. 37ft long and it rises 2.5ft from bottom to top. That's a 6.75% slope if I did my math right.
I do have a gravel pad beside the house. It's about 9ft wide for half the depth and it narrows to 8 ft for the rest of the depth.
If I end up with a 50's or early 60's airstream which is my hope then yes I would tuck it in and park it on the pad come winter. I don't think I'd be able to get anything newer down that narrow space.
Glad to know that I should be ok getting in the driveway though.
I won't have any town bylaw issues at all. My neighbor is great and the town really doesn't care a whole lot.