Front Hitch or Trailer Dolly?

I've got a 1987 17 Montauk Boston Whaler that I regularly take in and out on a single axle trailer. I'm having trouble backing into the spot given the # of cars parked on the street (especially if they are parked across) since my F150 + the trailer have very narrow clearances.

I'm wondering if it's better to get a front hitch or a trailer dolly in this instance? I have plenty of space on my own lot it's just the cars across the street make it difficult to pull in.

My boat parking spot has a small lip (not a 90 degree lip but a small ramp almost), which may make it difficult to push in my hand.