While partially successful, Taylor also experienced many of the frustrations subsequently felt by his successor Gordon Smith in the build-up to his sudden resignation from the job this week.
Now chief executive of Uefa Events SA, the independent marketing and business arm of European football's governing body which was set up last year, Taylor is a distant but interested observer of the latest developments in his former workplace.
But while Taylor has some sympathy with the widely-held view that the committee system which underpins the SFA presents a permanent road block to meaningful progress, he also has words of warning for those calling for drastic revolution within the corridors of power at Hampden.
As the SFA begins the process of seeking Smith's replacement, Taylor insists that too much dilution of the influence of committee members would leave Scottish football at risk of being run on dictatorial lines.
"Do you want more executive decision making or do you want more democracy, that's what you have to ask when criticising the committee system," Taylor told The Scotsman from his office in Nyon.
"You have to make sure you strike the right balance. Yes, the current system at the SFA can slow things down and doesn't lead to radical change. But you have to remember that those people serving on the various committees are all volunteers who have come through the system. The SFA reflects the whole nationwide structure of Scottish football.
"In Scotland, you have to make sure every part of the country is represented within the SFA structure. It's not the Strathclyde Football Association, it is the Scottish Football Association. You need to hear the voices and have the input from those involved in both every region and level of the game.
"Football associations all across Europe have committee systems, it is not something which is unique to the SFA. Look at the FA in England who have had quite a few issues in recent years and have gone through more chief executives than the SFA. Uefa itself has many committees. It is the committee system which allows for the democratic running of the game.
"The pace of change in football can be slow, but in a sense that is no-one's fault. Football has to govern itself and it needs consensus to make improvements. You need momentum to build change."
While the buck invariably stops at the door of the chief executive when it comes to public accountability, Taylor says the influence of the SFA presidency, currently occupied by George Peat, should not be under-estimated.
"What often remains overlooked is that the most important and powerful man in any football association is not the chief executive, it is the president," he added.
"When I was at the SFA, I had the help of two very supportive presidents in Jack McGinn and John McBeth and we did streamline the SFA to some extent. We reduced the size of the SFA Council, established the executive board of directors and speeded up some procedures.
"George Peat, who was a vice-president back then, was also supportive. It is not easy to effect the kind of change you think is necessary and obviously Gordon Smith found that aspect frustrating. But I wouldn't say the SFA is necessarily a council of despair. Regardless of what its critics may say, the SFA is a respected institution within many walks of life in Scotland and certainly throughout European football.
"So as far as I was concerned, it was a great job and it is still a job which many people will find attractive. There is a lot of frustration involved but a lot of satisfaction as well. The greatest satisfaction comes when the senior international team is winning matches. Those are the times when the criticism suddenly abates.
"I came to the job in 1999, just a year after the SPL broke away from the SFL. In the aftermath of that, there was a lot of resentment and even bitterness around. It was a difficult period. What the various bodies need to realise is that they are all in it together in terms of trying to do what is best for Scottish football. There are bigger structural issues which are more difficult to address. Henry McLeish has been looking at all of this in his review of the game and it will be interesting to hear what he has to say."
Hearts managing director Campbell Ogilvie, already in line to succeed Peat as SFA president next year, was among those who have been linked with the chief executive position. Taylor sees no reason why both roles could not be successfully integrated.
"At Uefa, Michel Platini is very much an executive president," observed Taylor. "It wouldn't be fair for me to comment specifically about Campbell Ogilvie or anyone else in those terms, but I can say that I don't think it specifically has to be a chief executive in charge.
"In Uefa, we separate the football administration from the business administration. Clearly, Uefa is a far bigger organisation than the SFA, but it shows that you can either combine or divide various tasks in different ways."