Come on. You're implying that not only is Mr Cash stupid but also he's a fool. If there are title issues he can't subsequently sell until these are resolved. So he is betting that there is a bigger fool out there who would buy a property with unresolved title issues. I'd suggest the supply of bigger fools is limited.Any planning issues for example can be accepted by a cash buyer, whereas solicitor would note title issues to Bank.
You imply that Mr Cash will overpay for the property, i.e. the asking price plus more later to fix the problem. That's one way to burn up his / her cash. If Mr Cash or any other purchaser, cash or otherwise, can see or suspect there is a problem, they overpay if they pay anything more than the market price less the estimated cost of fixing the problem. (Unless the market price already reflects the cost of repair.)No. Mr Cash will make a call and see that there is a problem with something and will decide they are willing to still buy the property with the idea of paying to get the problem fixed themselves.
Assuming Mr Cash is wealthy (which he / she probably is if they can make a cash offer), their marginal utility of wealth is different (i.e. lower) than of a person who has to borrow to make an offer. Well-off people, assuming they behave rationally, take risks only if the expected return is big. If there are problems with the property Mr Cash will make an offer only if he / she can get it at a deep discount. Otherwise why would he / she take on risk?