Robert Boag, who runs the UK Commercial Property Trust, stands out from his peers for his enthusiasm for selected retail property investments at a time of weak consumer spending.
But he is scathing about the capital's attractiveness as a retail centre.
He said: "It [Edinburgh] is left behind. It is a historic thing. I think it is a political thing."
Mr Boag argued that a focus on tourism had led to missed opportunities to develop Princes Street in the city centre.
"It has been all about protecting the heritage. Politically there were a lot of wrong decisions made."
Meanwhile, a number of shopping centres have been developed on the periphery of the capital and are attracting shoppers who might otherwise go into the centre.
He dismissed the idea that it was hard sympathetically to develop a city's retail offering while retaining its historic charms.
"Cambridge can do it. Bath can do it," he said.
Mr Boag contrasts this with Glasgow, where he is a senior investment director for Ignis Asset Management.
He said out-of-town shopping centres had been built around Glasgow but at the same time sites in the centre were redeveloped.
But he said: "In Glasgow you have got all those retail warehouses and shopping centres but Buchanan Street is where lots of retailers still want to be.
"Glasgow has been able to give retailers what they want," he added. "In the city centre you have got a retailing environment with a range of decent-sized stores that attracts a diverse range of retailers and you have got a population who have a degree of disposable income and they like to spend it."
Mr Boag's fund owns 41 properties across the UK, let to some 321 tenants.
It includes a property on the corner of Buchanan Street and Argyle Street in Glasgow occupied by HSBC.
Other investors have also recognised the investment charms of the area with the Strathclyde Pension Fund recently paying £35 million for most of the House of Fraser department store on Buchanan Street.
A recent report highlighted Buchanan Street as the sixth most expensive retail district in the UK with the second highest rents outside London at £250 a square foot and Mr Boag said it is one of few areas of Scotland where rents were rising.
Meanwhile, work has yet to get under way on the long-awaited project to demolish the St James Centre in the centre of Edinburgh and the completion date for the work has been pushed back to 2018.
A project to develop a tram network in the capital has been cut back and is running at least three years late.
Ross Martin, policy director at the Centre for Scottish Public Policy think tank, said that, in part driven by the economic downturn, policy-makers and business people were finally attempting to think about the role of Edinburgh city centre.
"I do not think anybody in the public or private sector in my lifetime has got to grips with it.
"But I think they are beginning to understand that there needs to be proper rational discussion and explanation about what that role and function might be.
"It has been forced on them by the economic climate because they have always been complacent about that."
Graham Birse, deputy chief executive of the Edinburgh Chamber of Commerce, added: "Edinburgh has been left behind and needs to punch its weight as a retail destination once again.
"A number of initiatives are under way to refresh the retail offer on Princes Street and the Henderson Global Investors St James re-development will represent the biggest investment in the city centre for decades.
"We are confident the direction is the right one, but we also need to face down the culture of community activism which can prolong the planning process and prevent development from creating the jobs which are so badly needed at this time."
