Should you get to the point where it is needed, there are commercial electric dollies which attach to the trailer via the hitch which are excellent in tight spaces and would probably be powerful enough to push the trailer up the driveway. An archive search will give some results.
Also, except for the dip, your driveway looks really good. We had or have a member (maybe others will help me remember) who had an amazingly scary driveway... very step downhill with a sharp curve! His avatar was epic!
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