ilmscore | I Was Sleeping at Work to Save, Now I Own 8 Rentals (EXPENSIVE Market)

I Was Sleeping at Work to Save, Now I Own 8 Rentals (EXPENSIVE Market)

Published: 2025-11-17
Status: Analyzed

Predictions from this Video

Total: 4
Correct: 0
Incorrect: 0
Pending: 4
Prediction
Topic
Status
Ben predicted he would be able to afford to live in New York for as long as he desired by owning property with a 30-year fixed rate mortgage.
"I knew I'd be set basically where I could make sure at a minimum I'd be able to to afford New York as long as I wanted to stay there."
New York Real Estate Affordability
Pending
Ben intends to continue working his W2 job while acquiring multiple Airbnbs to generate sufficient paper losses (through depreciation) to offset his W2 income tax liability annually.
"I'm gonna keep my W2 job. I'm gonna acquire as many Airbnbs as possible um and just make sure I'm maxing out those losses every single year on paper so I can basically offset my taxes."
Real Estate Tax Optimization
Pending
Ben predicts that the short-term rental tax loophole will persist for a considerable time, and he plans to continue utilizing it to maximize his tax benefits in the coming years.
"My strategy out into, you know, future years is to keep maximizing this loophole. Looks like it's gonna be around for a while longer, so I'll keep exploiting it as long as I can."
Real Estate Tax Loophole
Pending
The short-term rental tax loophole for tax write-offs against W2 income is predicted to remain available for a significant period.
"Looks like it's gonna be around for a while longer, so I'll keep exploiting it as long as I can."
Real Estate Tax Strategy
Pending