Wouldn't it be easier to back it in when you return from a trip so you can pull it out easily when you're ready to leave on the next trip?
My thinking is it's easier to back it in to the driveway from the street since you can pick your spot as far as timing the process and once you have the trailer partially in the driveway and the truck out of the street you can take your time getting the trailer line up how you want to park it.
I have a 32.5' travel trailer that I park in my drive. You can't back it straight in. When I get home from a trip I've got a 1/4 mile view up and down the road. I wait for a clear spot (no car in that 1/2 stretch) and get the trailer somewhat lined up so the end of the trailer is right at the entrance of the driveway. I back it into the driveway to the point where my truck is out of the street (takes about 20 ~ 30 seconds) and then, with no concerns about blocking traffic, I spend as much time as I need getting the trailer straighten up in the drive and leveled (3 ~ 5 minutes). Pulling out for the next trip takes all of 10 seconds.
