@sixdogs, Since there are substantial variations in starting draw amongst different motors/manufacturers, and especially with different loads (in this case the back pressure from the depth of the well and the house plumbing), and in the generator winding and overload control circuits, can I suggest that you borrow or rent a generator of the size/type you want to use to see if it meets your needs?
It just seems to me that once the discussion moves beyond "is it possible, at some point for one time?", the devil is going to be in the details, as above, and as well as other factors such as whether you have adjusted your generator to get the right voltage and frequency at the well pump.
I know enough cases where someone did manage to start a well pump a few times on their generator, only to burn out the generator windings after a half a dozen or perhaps twenty starts, so to me it is a horses for courses thing. Do you want to have this new generator start the well pump a couple of times, or do you want to be able to rely on it? What would be your backup if the generator that you are thinking of buying fails?
Just my $0.02... Good luck!
Peter