I am genuinely confused why we see projects like Tigerstedt block and this one proposed when there are surface parking lots nearby.
I think part of the dynamic is that it takes effort and skill on the part of landlords to cultivate successful commercial properties, and that means that those same landlords are actively thinking about whether it makes sense to redevelop all the time. On the other hand, if your REIT or trust or estate or whatever has owned a parking lot for 10 years, you may have no one thinking about whether it's a good time to sell or not.
I would love to hear other theories of why this happens.
Here's my theory/rant on this one:
My theory is that Calgary's development, form and culture is overwhelmingly set in post-1970/80s - much of the development and urban scene is overwhelmingly focused on a corporatist asset management model of where there's an imbalance between how many people/businesses want to be the asset owner and how many want to actually do stuff like run retail, open a bakery or intentionally curate commercial tenants. Everyone loves owning property, less people love running a business within it.
Most of the city centre has long had it's properties amalgamated and setup for redevelopment in this way where larger firms are playing the long-game of land banking, with seemingly little interest in what/who occupies the land in the meantime. It's very asset management inspired, rather than something more ground-up local owner/operator focused. The older inner city being proportionally small as it was overwhelmed by suburban expansion that went on to define Calgary 1980s through to today.
Compare that to a city like Toronto. Of course they have an absolute engine of asset management in property, but they have other factors where it's mitigated. Most critically and comparably to this 1st Street example, Toronto is famous for its retail main streets, any single of which dwarfs Calgary's main streets all put together in amount of properties, businesses and retail options. Hundreds of kilometres of street-front, pedestrian oriented retail exist stretching in all directions of the inner city. These streets are supported by tens of kilometres of high density low-rise housing, generating huge retail traffic on foot daily for over a century on every corridor. All benefits we can never have because we "grew up" in the late 20th century, instead of the late 19th century like Toronto.
This supply of commercial retail and the era of development does a few things. Firstly, ownership is fragmented into many narrow and small owner-operator parcels. Narrow buildings are cheaper for individuals to own - as fundamentally buying less space is the only tool for individuals to outcompete corporations and their access to capital in good locations. Huge, stable foot traffic from huge, stable populations nearby means that small footprint shops and retail can be good business. Unlike Calgary, there's less pressure to oversize your restaurant and "peak-hour" design things where you must catch the Friday and Saturday suburban tourist crowds or your business will fail. The daily local foot traffic is enough.
Another thing this successful small retail, narrow footprint model does is that even after a century of land consolidation, there's still many blocks with many different owners - no one can tear down and replace a whole block. When it does happen, it's met with a myriad of heritage preservation rules and restrictions which stall projects, raise the cost of housing, and ultimately preserves many retail frontages. That's not to say it can't happen - Toronto has lost dozens of retail blocks over the past century to major redevelopment schemes - but they also have thousands of similar blocks that haven't been touched.
A side effect that's really important is the culture of small-footprint retail and these main streets. Having so much identity tied up to it's main streets it also means Toronto developers often want to lean into that identity rather than away from it. Few developments in Toronto just ignore the existing building, even if they bolt on an 80-storey condo to the roof. And I don't mean just preservation of facades - even full new buildings that preserve nothing often have small, narrow retail frontages akin to what was replaced. What they are selling is an opportunity to live on one of these classic main streets with all it's little shops, not some shiny new thing that fully ignores the past (of course, all this is debatable as seen in Toronto development politics).
Calgary really has none of that natural defense against consolidation and redevelopment of old blocks. We have so few old blocks remaining (because we let so many be torn down), most sites are consolidated and we have little collective culture to preserve them. Folks describing this 1st Street block as "shabby", "not really original", "not actually heritage" etc. buy into that ideology. We don't really value old stuff and small, retail shops. Our density is increasing in many places, but mostly remains too low for small-footprint retail to be successful in most areas, forcing retailers/restaurants into that "peak-hour" design with larger footprints just to catch the weekend traffic so they are viable. Larger footprint requirements plays right into the hand of the asset management types - consolidate for bigger retail, bigger developments.
This long-running lack of interest culturally in small, commercial spaces links right into the rules we use to guide development. Our heritage and preservation rules are toothless, and most egregiously we allow surface parking lots in the inner city - it's the most pro-asset manager development rule we could ever come up with where we support land owners to only own for the purposes of owning, regardless of the impact on the community. Hell, even the new re-build McDonald's on 17th Avenue got it's drive-thru plays into this corporate-supportive attitude we have here.
TL;DR - Calgary's historic retail blocks suffer because we (as a city culturally, individually etc.) are more interested in supporting corporate asset management process rather than owner-operator retail processes. Unlike older cities we have less natural defense against redevelopment as we have such a minimal supply of heritage retail blocks. This plays out in a bunch of ways where we value heritage less and redevelopment more, most want to own an asset rather than operate a business, and we create rules that makes it harder to make choices that don't lean into these things. The result is continued redevelopment on old buildings, decades of land-banking for parking lots, and huge restaurants.