Hitch jack fully extended: Should I be nervous?

I'd be looking for a power tongue jack. It looks like your manual jack doesn't extend very far. My driveway is sloped as much if not more than the pic. Just put down as much wood as possible when the trailer is still hooked up. My power jack doesn't need to extend all the way to get it completely level. Don't forget to lower your stabilizers also to keep it more stable. I made cribbing from 2x4s screwed together for under the stabilizers. I also have 4 rubber chocks for in front of all 4 tires.