Adjuster here.
Your roofer is overstepping a bit, in my opinion.
I’ll start with the gutter. If there’s no documentation that the old gutter was damaged, there’s going to be no payment on the gutter. If there is documentation of damage, you’re now putting your date of loss back over a year (before you replaced the gutter). This could be a slippery slope, as some carriers will give you the cold shoulder if the damage is over a year old. Otherwise, it’s reasonable to assume the new gutters would be damaged by hail (I gather they aren’t).
Concrete: I have a hard time believing that concrete is chipped or broken due to hail. I’d have to see it, though. Generally, concrete gets what’s called spatter (the hail explodes and leaves a mark on impact), and that will naturally diminish, no payment needed.
Fence: If the fence is stained/painted and damaged by hail, it would be power washed and re-stained/painted. If it’s not, same as the concrete above.
Your roofer is making you a lot of promises that he isn’t in control of. Proceed with caution. Understand that this person is a salesperson, not a roofer. This person is likely paid on a commission-only basis, and that’s why he wants to ‘help you out.’
I have no idea if there’s legitimate damage on your roof or not. Some of the things I’m hearing make me suspect there isn’t.