Regarding the main weakness, I think you nailed it. That being said, one could make a pretty convincing argument to the home owner that by participating in suc

Regarding the main weakness, I think you nailed it. That being said, one could make a pretty convincing argument to the home owner that by participating in such a service, even at a premium, they'd actually save thousands of dollars. By keeping a home well maintained, you can avoid many of the big repairs that you'd otherwise be subject to. Most people don't caulk cracks when they first appear. They don't check their siding and roofing for cracks and leaks on a regular basis. They don't change out their furnace filter every winter. And a 100 other things they should be doing but aren't. And you're right - people don't budget for the big issues. And that's all the more reason they need a service like this. A monthly, predictable bill is more manageable than a series of big, one time hits. As for maintenance debt, pricing might need to take into account the age of the various components (roof, fence, siding, ect...). And, of course, any pre-existing conditions (ie. roof needs repaired now) wouldn't be covered at all.