Everyone who puts a lot of writing out in public is bound to want a few of them back. Quite a few of my takes have aged as well as a chip-chopped ham sandwich that got bumped to the back of the fridge and forgotten.

I was reminded of some of my greatest misses this week, when the Ferris wheel-anchored Esplanade mega-development on the North Shore finally broke ground. Back in 2023, I put it in my “Dead Developments: 10 promising Pittsburgh building projects that never happened.”  In my defense, I ranked them from Dead-dead to Undead, and this one was the closest to reanimating and shambling around. (The developer emailed me with annoyance back then and said it was still on track; I guess he was right). In the same story, the Garden Theater finally found suitable tenants — defying my predictions — though one (Starbucks) did just close.

It could be worse; I could be the guy who asserts that people who make $140,000 a year are actually poor, a contender for the Bad Take Hall of Fame. Or, I could have been a sportswriter, which practically requires taking indefensible positions all the time. They’ve got thicker skin than stegosaurs, particularly in this town. When I compared Kenny Pickett-to-George Pickens as “the next Montana-to-Rice,” I was trolling a Niners-loving relative, and not putting it in print for the world to see. Recently, I’ve been poking fun at the “FAAAHRR TOMLIN” guys for their all-purpose solution to the Steelers’ struggles — but maybe they were right after all.

I’ve said plenty of strange things in this column, mostly in jest, but one error I make pretty regularly is being way too optimistic about certain neighborhoods. I really do want Homestead, Hazelwood, and Carrick (among others) to become thriving, healthy places where working-class Pittsburghers can get ahead. And I do honestly think these places have a lot going for them. But I’m often way off on the timetable, as with the Esplanade.

For sale: 1605-1609 Brighton Pl., Mexican War Streets, $500,000.

You don’t see a lot of side-by-side triplexes like this for sale, and … wait, this one just dropped by $170,000 — what in the name of Zarley Zalapski is going on here? This column is definitely not aimed at prospective landlords, but you could comfortably house most of a hockey team here, so maybe do that instead. Also, we’ve got purple walls in at least one unit.

606 Middle St. Credit: Courtesy of Zillow

For sale: 606 Middle St., Deutschtown, $294,000.

That is a lot of historic (circa 1900) house for not a lot of money in a neighborhood that turned the corner quite a while ago. It’s a duplex, even, and just dropped by $5K. So, what’s the catch? The catch is, um, EVERYTHING ELSE. You wanted lower prices? Well, OK; elect fools —> cause recession —> everything is cheap now because everyone feels poor. So much winning!

Schoolhouse Apartments, 500 Tripoli St. Credit: Courtesy of Zillow

For rent: Schoolhouse Apartments, 500 Tripoli St., Deutschtown, $1,450/month.

I  know what you’ve been thinking: there simply aren’t enough places in Pittsburgh for rent with spiral staircases protruding from the wall. Well, fret no more; the Schoolhouse Apartments, one of the first school-to-housing conversions in town, has you covered. Most price points here are a bit higher, but nothing out of the ordinary for Pittsburgh in late 2025.

1326 Woodland Ave. Credit: Courtesy of Zillow

For sale 1326 Woodland Ave., Marshall-Shadeland, $190,000.

OK, now I think I’m being trolled. My most consistent take is that the weird mid-century mania for creaky aluminum awnings should be shot into the sun. So, here’s a duplex that’s mostly metal awning; what are we even doing here? Hey, if you’d like every rainstorm to sound like a hundred chipmunks dancing the rhumba in cleats on your roof, go for it, I guess.

Greenhill Apartments, 4221 Winterburn Ave. Credit: Courtesy of Zillow

For rent: Greenhill Apartments, 4221 Winterburn Ave., Greenfield, $1,145-$1,265/month.

What was going on in the ‘70s? (Besides drugs, I mean.) This probably started out as a mansard roof, but now it looks like an unflattering haircut — Lord Farquaad from Shrek, maybe — which isn’t really a thing that any apartment needs. (Stay tuned for my next column idea, “houses that resemble one-joke cartoon characters.” Since Pittsburgh largely stopped building housing in the ‘70s, the Greenhill Apartments are still technically on the newish side for us.

5440 Fifth Ave. Credit: Courtesy of Zillow

For rent: 5440 Fifth Ave., Shadyside, $1,250/month.

They’re not building any more Shadysides, a.k.a. dense, pedestrian-scaled neighborhoods with a vast array of housing options, from Victorian mansions to kind of tired mid-century apartment buildings, at a surprising range of price points. There’s lots of reasons for that, starting with single-use zoning and the ever-profitable prioritization of cars over people. But we built neighborhoods like this before, so we probably could again.

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