This is jmo, but I wouldn't even consider buying a house with a pool that needed that much work. I'd be afraid that it could turn into a real money pit. An allowance for something like that isn't enough assurance because there are too many potential problems that could be unseen. If cash is an issue, I'd look into a home equity loan to do a proper, complete repair and then sell. You'll sell faster, and for a better price. Best of luck either way.