In October 1989, after viewing the new Weatherfield Quays dockland development, Audrey Roberts decided she'd had enough of living in a backstreet terrace and put 11 Coronation Street on the market. Mr Simpson valued the house at £25,000 and assured Audrey, who was eager to sell and move up in the world, that there was a demand for "terraced cottages", especially by first time buyers and retired couples. Although Audrey had set her heart on getting a dockland flat, Mr Simpson tried to interest her in their other properties, which according to him were just as nice. His spiel was challenged by Alf Roberts, who didn't want to move and didn't believe anyone would pay the asking price. Just two days later, Jim and Liz McDonald saw the advert in the estate agent's window and offered the Roberts the full asking price for the house.
Seven months later, Simpson & Simpson were contacted by Newton & Ridley, the brewery which owned the Rovers Return, to offer £30,000 for 1 Coronation Street so that they could extend the pub, which was set to be renovated and rebranded as "Yankees", a New York-style theme bar. After receiving two letters from the estate agent asking her to sell despite the house not being on the market, Deirdre Barlow was intrigued but worried about the fact that the buyer was anonymous. Mr Simpson visited No.1 to assure Deirdre that it was a genuine offer, but Deirdre remained curious and refused to accept unless she knew their identity. On a subsequent visit, Mr Simpson allayed her main worry - that the offer had come from Ken, playing some kind of game - and revealed that the buyer was Newton & Ridley. As the brewery had said publicly that the changes were off, Deirdre was sworn to secrecy, although Simpson's lack of discretion was criticised. Mr Simpson paid a third and final visit to No.1 a few days later to hear Deirdre's answer. Out of loyalty to Alec and Bet Gilroy, Deirdre turned the offer down, but was talked into a meeting with a brewery boss at the Coach and Horses. Mr Simpson advised her to go on the basis that the brewery may increase their offer. Ultimately, Deirdre accepted £35,000 for No.1, but Newton & Ridley cancelled the sale when Cecil Newton came out of retirement to quash Nigel Ridley's theme pub idea.
Mr Simpson's last visit to Coronation Street occurred in July 1991, when Emily Bishop decided to sell 3 Coronation Street and retire to Rhos-on-Sea. Mr Simpson went through the arrangements with Emily, telling her that she would pay the estate agent 1.5% of the asking price. Upon learning that Percy Sugden lodged with Emily, Mr Simpson asked if he had a formal tenancy, warning her that it could lead to complications. Emily told him that there would be no complications, at least on that score. Emily took the house off the market when she realised that what she wanted wasn't a change of scenery, but a change of lodger!
Mr Simpson's estate agent was also hired to sell 17 Elmgate Gardens, widow Jackie Ingram's marital home which she decided to sell so that she and lover Mike Baldwin could have a place which was 'theirs'. Having been dumped for Jackie by Mike a few months earlier, Alma Sedgewick viewed the house under the name of 'Mrs Halliwell' (Halliwell being Alma's maiden name). Alma wasn't planning to buy and went to the house for no reason other than curiosity, but when Mr Simpson's sales pitch was interrupted by a phone call which took up his attention for several minutes, Alma went into Jackie's bedroom where, in a moment of madness, she slashed the duvet with scissors. After her handiwork was discovered by Jackie and Mike, Mike went round to the shop in a rage to demand an explanation from Mr Simpson. Simpson refused to discuss the matter at first, as he didn't know who Mike was, but when a furious Mike dropped a duvet slice on his desk, he lost his composure and gave Mike a description of the woman who had viewed the house - thin and dark, with big, striking eyes. Realising that it had been Alma, Mike stopped Simpson from calling the police and went to handle the situation himself.
Though normally business-like in his manner, Mr Simpson occasionally showed a more personable side, such as when he commented to Tracy Barlow, when she went upstairs to play her tapes, that he would rather listen to Kylie Minogue if he had the choice.