I'm not an expert in solar panels by any stretch, but my understanding that the two major breakthroughs we need are a) how to make the solar panels themselves more efficient over a long life-span. Typically they lose 2-4% of their efficiency every year, meaning 20 years down the road, they've lost 50% of their energy power. b) a more efficient converter from the DC generated by the solar cells to the AC we put back into the grid.
In others words, design it with replacement by do-it-yourself homeowners in mind. I looked up the spec for one and it was 1250x800 mm (~4x3 ft) and weighted 12 kg (~25 lbs). That's a little awkward for one person to cart up a ladder, but what if they were half the size and had a strap handle on the side? What if they used quick disconnects for mounting? If you set out with these as design goals, then I'm sure a feasible solution could be found.
Smaller panels can make it easy to replace gradually, acouple here, a couple there...
In practice such things are not common at all, people don't have friends who will just go up on roofs and do serious work. The best you can hope for is something as easy as installing Christmas lights (which doesn't even require getting on the roof itself, just up to the eaves).
$1000 every two years is less than $50 month.
I'd happily pay $50/month for all my electricity.