That's true. But if the next generation did not have to build their own houses it would give them a 'dividend' passed down by the previous generation and that wealth would ultimately give them more economic freedom and fewer opportunity costs.
Then with those advantages, any problems will be easier to face, such as starting from the pile of dirt again.
Otherwise each generation is constantly facing the same struggles with paying the rent.
Also consider, and I think this was implicit in what the OP was saying, that closed loop systems might make many existing problems relating to maintenance obsolete. So the next iteration of building might take place in two or four generations from now instead of for each one.
Sadly truly effective maintenance free filter technology appears to be holding closed loop systems development back. I know Kamen was trying to build a Slingshot mechanism but so far as I know this has not bourne any fruit. This is the kind of unsexy, hard stuff that Silicon Valley need to be pulling together.