The question is also who will be left holding the bag. If title searches over the past 10 years have turned up nothing problematic, then likely when the flipper sells, their buyer's title search won't turn up anything either.

And once their eventual buyer buys the house, it's their problem (not the flipper's) -- well, their title insurer's problem -- if a title dispute comes up later.

And given that the flipper's goal is to hold the house for a relatively short time and make a profit on the improvements, a thousand or few saved on the title insurance could actually be a material amount of that profit.