How old/infirm are you guys? I'm old and retired, and would just wait till a non-windy day, tack a 2x6 on the rafter tails as a stop, and walk up a step ladder and throw the panel onto the roof. 7/16" OSB weighs less than 50 pounds, easy to handle if no wind.
This is a shed, looks to be less than 10 feet off the ground to the tails. An 8 foot step ladder, walk up half way, and set the panel on the roof. Or lean a conventional ladder onto the 2x6 stop, push the sheet up ahead of you, and it'll flop onto the roof when it goes over the top of the ladder (like Mushcreek showed). Not a difficult, nor dangerous job. I recently roofed my house like that; and it's 8:12 and about 12 feet to the lower roof. I used a safety harness and rope once I was actually working on the roof; both OSB and synthetic underlayment can get slick, particularly if they get a bit of sawdust on them from trimming the sheathing in place.
As others said, the shingles will be as hard or harder to place up, you have to climb further up the ladder.
If you're infirm or weak, then get someone else to help, or to just do it for you. 8 or 10 sheets total it looks like, roughly a 15 minute job to get them onto the roof and can be distributed from the initial location after that.