By: Guillermo Salazar • 04 March 2025

Four Property Managers: Longing for the golden age of Property Maintenance

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One Screwdriver, Two Biceps, Three Trips

(I re-heard Monty Python’s Four Yorkshiremen with my kids over the weekend and couldn’t stop reimagining it in the world of maintenance. Enjoy the laugh. Hope this gets some people thinking as we head into #Retcon in Vegas next week)Property Manager 1: Aye, remember the good old days when we only had a single rusty screwdriver for the entire complex? Now that was real property maintenance.Property Manager 2: Luxury! We managed three buildings with nothing but a bent flathead and a ring of keys so big it made our tool belts sag to our ankles. And we were grateful for it!Property Manager 3: Grateful? We covered five properties with a roll of duct tape, a well-worn socket (we never cared if it was metric or imperial), and a skeleton key that only worked if you jiggled it precisely fourteen times. Tenants loved that bit o’ excitement.Property Manager 4: Keys? You had keys?! We memorized where each tenant stashed their spare under doormats or garden gnomes—then walked uphill (in the snow, mind you), carrying a bag of various sockets, none of which fit the actual bolts. And we called that a holiday.

The Glory of the Key Ring

Property Manager 1: Ah, the sound of a well-stocked key ring clinking against your hip—nothing like it.Property Manager 2: Right! And when you needed to open a door, you’d start cycling through keys, one by one, until—click!—success, usually around key #43.Property Manager 3: 43?! That’s efficiency! We had so many keys, we had to carry them in a small duffel bag. Used to set it down for a second, and the weight would pull it right through the floorboards.Property Manager 4: Keys?! We had a single master key for the entire building… except we never knew which building it worked on. So, every lockout was an exciting game of “Guess Which Property We’re Breaking Into Today.”

A Masterclass in Work Orders

Property Manager 1: Work orders were beautifully simple back then. Just a quick handwritten note on a coffee-stained napkin—straight to the point!Property Manager 2: Aye! None of this digital nonsense. If you were lucky, the tenant left an actual description.Property Manager 3: If you were unlucky, you got something like “Sink broken”—no explanation, no details, no clue which apartment.Property Manager 4: Sink broken? Luxury! We’d get notes like “Water everywhere” scrawled in panic. Could’ve been a leaky faucet, could’ve been a biblical flood. The fun was in finding out!

The Toolbox of Champions

Property Manager 1: Oh, but it kept us on our toes, didn’t it? Why, I recall changing out a doorknob using nothing but a butter knife and sheer determination, all while the resident peered over my shoulder like I was Michelangelo painting the Sistine Chapel.Property Manager 2: You had a butter knife? Luxury! We had to use the back of a spoon, borrowed from the tenant’s cupboard—if we were lucky! Usually, we just chipped away at screws with a pocketful of hope and the tip of a clipboard.Property Manager 3: Clipboard? Blimey, that’s fancy. We wrote all our maintenance requests on used napkins—never had actual forms, you see. We’d lose half the napkins in the back of our van, so every job came as a surprise.“Oh look, a scribble about a clogged sink from 1987—best get to it!”Property Manager 4: A van, you say? We had to haul every tool we owned—namely one battered hammer and a squeaky pair of pliers—in a tattered cardboard box strapped to a bicycle. And the bicycle had no seat! We’d pedal across the property, the wind in our hair, sockets rattling loose, and we’d consider it downright blissful.

Multiple Trips: A Testament to Dedication

Property Manager 1: Nowadays, people go on about “one-trip” fixes. What a shame!Property Manager 2: Aye! In our day, a single job meant at least five trips:
  • Trip One: Check the problem.
  • Trip Two: Bring the wrong screwdriver.
  • Trip Three: Fetch the right socket, realize it’s metric instead of imperial.
  • Trip Four: Return with the right tool but forget the replacement part.
  • Trip Five: Finally, finally finish the job—unless you had to go back for WD-40.
Property Manager 3: WD-40?! You had supplies?! We had to breathe on a rusty bolt and hope for the best.Property Manager 4: Breathe on it?! We just waited for corrosion to take its natural course, then congratulated ourselves for being patient.

The Measured Pace of Maintenance Excellence

Property Manager 1: None of this “quick resolution” business—quality took time.Property Manager 2: Aye! We once took three days to replace a doorknob. Not because we were slow, but because we respected the process.Property Manager 3: Oh, absolutely. You don’t just rush into a repair! First, you assess the situation. Then you think about it. Then you check your schedule. Then you—Property Manager 4: Forget about it completely until the tenant calls again?Property Manager 1: Exactly! And when we finally arrived, the tenant would say, “Oh, I thought you forgot about me.” We’d just smile and say, “Nope! Just ensuring we had the absolute best solution.”

Solving Problems Without Even Going On-Site

Property Manager 1: Nowadays, you can fix half the problems remotely.Property Manager 2: Unbelievable, isn’t it? Tenant calls, says their AC’s not working, and instead of driving over, you just say “Lets see if it is turned on to cool?” and boom—problem solved!Property Manager 3: In our day, we had to go in-person. Didn’t matter if the problem was as simple as “The lightbulb is out.”Property Manager 4: Aye! And you had to do it with dignity! “Oh, the fridge isn’t working?” Walks in, plugs it back in. Walks out like a hero.

Why No One Wants to Do Maintenance Anymore

Property Manager 1: You know what’s sad? No one’s going into maintenance anymore.Property Manager 2: Aye! Back in our day, we dreamed of a solid career in maintenance. Nothing more fulfilling than wrestling with a rusted pipe while a tenant watches in terror.Property Manager 3: And now? The younger lot—don’t want to get their hands dirty!Property Manager 4: Too busy staring at screens! “Oh, I want a remote job!” they say. Remote job? We were remote workers before it was cool—only difference was, we had to drive there, break a sweat, and then come back three more times because we didn’t know what we were walking into!

A Life of Adventure!

Property Manager 1: Aye! The thrill of the unknown—every maintenance call was an ambush! You’d show up expecting to fix a leaky faucet, only to find the tenant standing ankle-deep in water, shouting, “I think it’s getting worse!”Property Manager 2: Or you’d get a work order that just said, “AC not working.” You’d arrive to find a unit that hadn’t had a filter change since the Carter administration.Property Manager 3: And then there were the mystery smells. No context, just a note: “Something stinks.” That was it! A scavenger hunt for rotting food, dead rodents, or—if you were really unlucky—both.Property Manager 4: But that was the fun of it! No two calls were ever the same. You had to think on your feet! Now, they want diagnostics and automated alerts. Where’s the adventure in that?

The Lost Art of Hands-On Learning

Property Manager 1: Aye, and back then, we didn’t have “ergonomic” tools. You gripped a wrench so hard your fingers locked up for a week. That’s how you knew you were doing it right!Property Manager 2: But now? Oh no, my work-life balance! Oh no, my back hurts! Oh no, I have to wear knee pads!Property Manager 3: Knee pads?! We didn’t have knee pads! We had knees! And if they wore out, well, that’s why you had two of them!Property Manager 4: Aye… and now no one wants to do the work. Instead, they sit in air-conditioned offices, “managing” buildings instead of fixing them.

The Tragedy of the Labor Shortage

Property Manager 1: And that’s why there’s a labor shortage. Kids these days want easy jobs. But you know what? They’ll never know the joy of a screwdriver that fits perfectly on the first try.Property Manager 2: They’ll never know the satisfaction of opening a door on the first key!Property Manager 3: Or the pride of fixing a leaky pipe using only duct tape and sheer force of will!Property Manager 4: Instead, they’re out there saying, “Oh, we’ll just let AI troubleshoot it!” AI?! What’s next? A robot that shows up, stares at the leak, and sends you a text saying, “It appears your sink is dripping”?Property Manager 1: Aye! Then what?! A chatbot replacing us?Property Manager 2: Oh aye, and pretty soon, AI will be telling tenants, “Your maintenance request is very important to us,” while we sit here waiting for the work to come in!Property Manager 3: We didn’t need AI! We had instincts! If a pipe was rattling, we knew if it was about to burst or just saying hello!Property Manager 4: And that’s why we carry on. One manual screwdriver turn at a time.

What Ever Happened to Stanley Dewalt?

Property Manager 1: You know who didn’t appreciate the simple ways? Stanley Dewalt.Property Manager 2: Aye, Stanley! He was always rambling on about his battery-powered screwdriver—couldn’t stop talking about “efficiency” and “saving time.”Property Manager 3: Madness! He once brought his cordless witchcraft to a maintenance job, and we thought he’d lost his mind!Property Manager 4: Aye, we tried to talk sense into him. Told him, “Stanley, you’re gonna lose yourself in all that power. Maintenance work isn’t about speed, it’s about the journey!”Property Manager 1: But he wouldn’t listen. No, he was obsessed with those machines. Said he was heading to Milwaukee to make his fortune.Property Manager 2: Milwaukee?! He was chasing a dream! Said he wanted to revolutionize maintenance—standardize, automate, improve efficiency, build an empire!Property Manager 3: And what happened to him?Property Manager 4: Never heard from him again. Some say he made it big. Others say he just… the power went to his head.Property Manager 1: Aye, poor Stanley. Said the cordless drill would make work easier—but what happens when work gets too easy? What happens when the jobs start finishing themselves?Property Manager 2: That’s right. We saw it clear as day: one moment, it’s a drill replacing a screwdriver. The next, it’s a robot vacuum cleaner!Property Manager 3: And then? Then they don’t need us anymore. Machines tightening bolts, replacing filters, changing locks.Property Manager 4: Aye… and that’s why we stayed true to the craft. To manual labor. To proper tools.

Toast to Glory!

Property Manager 1: Aye, life was simple then. Screwdrivers were screwdrivers, keys were keys, and if a screw felt tight, we just turned it harder.Property Manager 2: Indeed. We cherished our well-worn tools like family heirlooms—full of history, character, and the occasional missing handle.Property Manager 3: Let’s raise a toast to those days—when a clogged filter kept us happily occupied, and we’d head home with a closed work order.Property Manager 4: Aye, to reliable screwdrivers, trusty key rings, and the fine art of multiple trips! Life had its own rhythm back then, and we embraced every moment.Property Manager 1: And to Stanley Dewalt—wherever he ended up.Property Manager 2: Aye, poor fool. Left it all behind to chase after his Ryobi dreams.Property Manager 3: He thought he could Bosch his way to the top.Property Manager 4: But in the end, he was just another Makita who lost his way.Property Manager 1: And now, we carry on. One manual screwdriver turn at a time.They clink their seasoned tools together, recalling those simpler times—and the genuine satisfaction of a job done with patience, confidence, and just a touch of everyday adventure.

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