Nobody is saying it's not frustrating. Quite the opposite. What we're saying is that whining about the City is misplaced. The reference to "the City, its agencies, and other corporations if publicly regulated" (as if they and their services are all the same) doesn't make a huge amount of sense, given the range of below-grade services, the actors involved and the different statutory and regulatory regimes - complicated by the fact that so many of the utility cuts are from the likes of Rogers, Allstream, Bell, etc., which the City has little control over beyond a permitting system. A recent City report estimated the telecom utility cuts total to be 40,000+ in any given calendar year, and that's before you even get into issues like watermains. The issues and players are such it will take way more than just sending everyone a memo saying "do better". Asking "how to get underground infrastructure right the first time" completely misses the point, because of the nature of the work and improvements and rapidly expanding infrastructure. It will never be "right the first time", as many of these services are constantly being upgraded and expanded.
Is it a problem? Of course. Can we manage it better? Certainly, although the difficulties are many, and some of them are even constitutional in nature. It isn't just a Toronto problem - jurisdictions elsewhere deal with it too, and just because you don't necessarily notice the utility cuts when you are on holiday doesn't mean that they aren't happening or that other trade offs have not been made to avoid them. The solutions (and there will be many, since it is a multi-faceted issue) undoubtedly require more money. That comes from somewhere - one's taxes, one's utility bill, one's internet bill, etc. Where's the groundswell of people wanting to pay to see fewer asphalt utility cuts? Was that an issue in any of the previous municipal, provincial or federal elections? You can understand where this issue lands on the list of priorities for most public authorities.
We need to stop thinking about the road allowances as being for vehicular and pedestrian traffic above grade, and start thinking about them as a shared space that also accommodates a highway of various services below grade, ranging from sewage to fibre optics. Obviously we need to better manage the competing demands for this space, but complaining that we are not properly "running the city", as if the issue is that some key people at city hall aren't on the ball, isn't going to lead us to a solution.
I've always felt that this issue is part of a much larger issue respecting how we value and treat the public realm in this city and in this country. We don't do a good job at it, and that has less to do with the responsible public authorities, and more to do with the public itself which doesn't demand better. Managing utility cuts better is more likely to come about when we start insisting on better streetscapes generally and making it a political issue. Until then, we can expect Bell to be ripping up a new sidewalk.