MIke,
Go over along route 20 between Charlottesville and Madison and you will see a number of those old barns painted and repaired by us. Use to help my dad and uncles do that when I was a lad. From what I can see in the photo you have more problems than paint! But it may just be the picture?
Those standing seams roofs will last forever? If they are taken care of. If you decide to do it yourself, be sure and check for rust, wire brush them, and use a good commercial red primer. Spraying is faster, but brush and roller will last a lot longer. You didn’t say anything about color? They make special paint for that type of roof, has the aluminum in it which makes it wear longer.
Looks like there is some damage there in the valley. If it's been like that very long, plan on replacing the planks under it. Repairing it is not much of a job, feel sure you could handle it; it does require some special tools. If you can't borrow them, might be cheaper to just get someone to fix it.
Also looks like that tree has some branches rubbing on the roof. Don't take long at all for a branch to damage a rib or rub a hole in the tin. leaves whole moisture and dirt which will lead to rust-out. One thing about tin roofs, they don’t that well to stuff laying on them.
The best way (and safest) is to work a 10-12 ft section of the roof at a time. Use ladder hooks (chicken ladder) along with ladder jacks; with a pitch as high as yours tie the ladders off over the top and use a safety harness. We used a mountain climbers rig, was cheap and we already had them. use two ladders, with a 2x12 between them.
I wouldn't wait until summer; you will be like dogs on the grill.
Hope that helps.
be careful
JD