You'll have plenty of space to make that back.
Out of curiosity I measured my driveway and street width.
The street is 23' wide and my drive is 17' wide.
My truck + TT length is approximately 55' and I can navigate that easily without hitting the curb on the opposing side of the street. (most of the time :))
You are correct in your approach, coming from the right to left. Back down the center of the street aiming the left side of trailer to get close to the pole.
Trailer tires will be a pivot point.
Be conscious of tail swing.
Ive backed tens of thousands of trailers up and all I can say is practice, practice, practice.
You'll develop a sixth sense as to where the trailer tail is the more you back.
In trucking we have a saying, Get Out And Look, G.O.A.L. if in doubt.
Here is a video of me bringing home our new trailer.
https://www.youtube.com/watch?v=c83uiWrOZy8
(I dont know how to get the vid to direct link, so you'll have to copy and paste)
The dimensions of my back are a bit different from yours but with a wider street and 9' of sidewalks you'll have plenty of space.
