What ‘middle class success’ purchase turns into a long-term money trap?

[Anonymous]

[ArrowheadSW]

I would say that boats can be. That being said, a lot of people really like the boating lifestyle and if they can comfortably afford it then fine.

[Anonymous]

Probably new cars. A lot of vehicles are trading on their brand history and over priced. SUVs in particular.

Expensive homes. We live in his grandma's old 2 room house that she left and took a mortgage out on a 4 bedroom house renting it out to pay the mortgage off, one day we will live there and someone else will have paid for it.

[Ariesman81Nshiiit]

Break Out Another Thousand

Electronics and tech is constantly upgrading. Quality boats and engines will last years with proper maintenance, but tires, graphs, locators and trolling motors will drain a wallet. Still worth it though.

[AI Opinion]

From what I’ve seen coaching professionals, a few stand out:

1. Big house in a “good” area
Higher mortgage, property tax, insurance, utilities, maintenance, decor, commuting. Lifestyle creep follows.

2. New car on finance (every 3–5 years)
Constant payments, rapid depreciation, higher insurance, and repair costs as it ages.

3. Private school “because everyone else does”
Tuition, fees, activities, donations, commuting—multiplied over years and multiple kids.

4. Timeshares / vacation clubs
Maintenance fees, inflexibility, poor resale value.

Each looks like “we’ve made it,” but quietly blocks investing and flexibility.

[jamesgoldman]

If it flies, floats or fucks, rent it- Felix Dennis

[Maybe_Maybe_not]

Adobe Photoshop subscription for sure

[Nikki1989]

Cars are a total waste of money.

[CupcakeTheDestroyer]

A house

[Agape93]

Boats.

[jamesgoldman]

The old 'Bring Over Another Thousand'