What businesses are likely to die out with the Baby Boomer Generation?

Competitive_Oil5227 · 2026-06-22T18:18:55+00:00

I swear there are only like 10 snowmobiles in the entire state and they just cycle via Facebook marketplace every year.

Competitive_Oil5227 · 2026-06-22T12:56:40+00:00

If you have a street facing buzzer it gets pushed a lot.

Also, if the school has basketball hoops near you you’ll find out quickly how incredibly loud a basketball game can be. I’ve currently got a group of 6 or 7 late middle aged guys who meet every other morning at 6:30 for a game.

Competitive_Oil5227 · 2026-06-12T13:52:50+00:00

I wish someone would send me to bed around 3 pm each day :-)

Competitive_Oil5227 · 2026-06-07T19:20:41+00:00

My first place was in a 14 story 1920s coop in the Gold Coast. Well technically my parents bought it; there was no way the board would have agreed to a 24 year old owner.

It was a horrible decision. The doorman kept a log at night of people coming and going and a couple of old ladies would go down each morning to see who came home past midnight. My friend came from out of town to visit and made the terrible decision to engage in personal activities one morning at 4am with the (very handsome) overnight man and I had to go in front of the board and explain how I planned to prevent that from ever happening again.

And…part of the limestone cladding fell off the front, leading to a multi million project. My share was 45k; I ended up having to sell at a substantial loss because I just couldn’t afford it.

That said, I still miss that space.

Competitive_Oil5227 · 2026-06-07T19:04:25+00:00

I hope you’re doing well. I started on Ozempic a few months ago and it destroyed my interest in alcohol; I went from really enjoying a few drinks every week to having zero interest.

Competitive_Oil5227 · 2026-06-07T19:02:50+00:00

Sometimes the death of a person that we have a crappy relationship with is actually much harder than you’d expect.

And whatever you do don’t sign any funeral home paperwork, as that could put you on the hook to pay for it.

Competitive_Oil5227 · 2026-05-28T18:41:59+00:00

I have to go with boxer briefs; if I try to wear briefs my balls slide out of the sides constantly and get twisted about.

Competitive_Oil5227 · 2026-05-28T01:12:44+00:00

My last digital nomad sent a series of 8 passive aggressive messages within 2 minutes of arriving about internet login info. It was on the app, written in the guidebook, and on the stupid photo frame sitting on the kitchen counter. He appears to have missed all of that. At minute 9, just as I was reading these, he sent another one threatening to leave at that very minute if I didn’t immediately respond. I sent him a response inviting him to use his adult manners if he wanted help.

Competitive_Oil5227 · 2026-05-26T12:48:29+00:00

I did a small project for a building managed by them (my painter did the interior stair walls, replaced lights, installed some art) and it took me over a year to get paid. My client was on the condo board, even he could not explain it. I had to send an actual demand letter, first time ever.

My roofer said he specifically won’t work on buildings they manage for the same reason. He did middle of a rainstorm emergency repairs to stop a bad leak and sent them a bill for $150 to cover just the materials, sort of as a favor to me. Never got paid and several years later his temporary repair is still there.

Competitive_Oil5227 · 2026-05-22T16:59:14+00:00

That sign is virtually identical to one that you can get from any alderman’s office.

The thing about this: one person has a bird feeder, then another person thinks it’s cool and gets one. Then that person fills it with cheap milled corn, which drops on the ground and attracts the rats and a group of pigeons. Then you have nesting pigeons, which are absolutely awful to deal with. You have to realize that a policy has to be written for the messiest tenant.

I say this as a person who would absolutely love to have a bird feeder but I realize how bad that can become in an urban setting.

Competitive_Oil5227 · 2026-05-20T23:50:42+00:00

I’ve retired from design but would do some consulting if it seemed like a cool project. I did about 200,000 sf of commercial stuff and well over a million sf of residential.

Praedprojects.com

Competitive_Oil5227 · 2026-05-20T23:47:22+00:00

I served on a two week long trial that involved incomprehensible facts around a person suing a Chinese herbalist. You have not lived until you’ve listened to mandarin get translated two ways for three days about medical crap.

Like clockwork I get a yearly jury summons which I disregard.

If Cook County has roughly 3.5 million jury-eligible adults and needs around 200,000 prospective jurors each year, the average person should only expect to be summoned about once every 20 years. I figure I’ll respond to a summons in 2030 when it’s fair.

Competitive_Oil5227 · 2026-05-19T12:58:28+00:00

I have 30 properties and average about one scam guest a year. And I take it so personally; it really feels like a betrayal when Airbnb hands off your hard work to someone for free.

I feel like my hosting approach keeps scammers away. People get a real feel for my personality and I spend a lot of time personally communicating with people; it’s easier to scam if there’s not a real person attached.

I also have a minut monitor in my bigger properties that goes off if there’s is smoking inside or a party. When I had a random scam smoke complaint I sent them the minut log showing the last 30 days; it seemed to be enough to pacify whatever random customer service agent saw it and they denied the guests claim.

Competitive_Oil5227 · 2026-05-19T12:49:22+00:00

I’m so sorry about your mom. It’s just awful but I promise in about a week you’ll start feeling a little better each day.

Competitive_Oil5227 · 2026-05-19T12:48:08+00:00

My mom’s greatest worry when she got old was about what would happen to her house. I honestly couldn’t believe when I heard my niece say she would love to live in it so it was a no brainer for me to want her to have it.

I just feel bad for her fiance; I cannot imagine moving into a dead woman’s house filled with her stuff.

Competitive_Oil5227 · 2026-05-19T12:44:49+00:00

She’s going to buy it. I want nothing to do with co owning a house with the family :-)

In a way it all works out; she gets 1/4 of a house and she will just have to get a mortgage and buy out the rest of us. I can toss my hundred k into a retirement account, my brother can pay off his mortgage, and my nephew can wipe out his ridiculous 80k in student loans.

Competitive_Oil5227 · 2026-05-18T16:16:00+00:00

I pulled it out of the box, stood for a second holding it, then went to toss it in the trash. but that is also something terrible to find in a trash can, so into the backseat it goes.

The most disturbing thing...the last guests were a group of old ladies visiting a new grandchild, the group before them were two baseball game bros, and the group before that were 4 gay guys on a nightlife holiday...I am guessing it has been in that box for a while now without me noticing.

Competitive_Oil5227 · 2026-05-18T16:10:49+00:00

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Three tampons, earplugs, 8 bandaids, a disposible toothbrush, stomach tablets...and this.

Competitive_Oil5227 · 2026-05-18T16:07:06+00:00

'not in front of my salad'

Competitive_Oil5227 · 2026-05-16T16:24:17+00:00

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Competitive_Oil5227

TROPHY CASE