hey husker, you'll get a much better response posting this in the WJ section...
I drive a TJ so take it with a grain of salt, but later TJs have a problem with the fuel spout, except the opposite, i.e. NOT shutting off
I would suggest next time instead of jamming the filler all the way down, pulling it back a notch...or vice-versa if it has been not going all the way in, jam it down. Sometimes it seems like there is a sweet spot that you have to hit.
The second issue sounds like what I think is called the check valve. Regardless what it is called, it holds fuel in the system, so that the pump does not have to prime the lines every time. If it is a slow leak, you may notice that after only a short period of engine off, it might fire right back up on the first try, whereas overnight you have to prime it. In the meantime, she probably doesn't need to turn the key repeatedly, but turn it once for 3 seconds, then try to crank it.
That's all I can tell you - repost in WJ and I'm sure you'll get a lot better help/details on your problems.