I know the short term rental market is hot and am wondering what's the best way to start out.

If you send me your email I can send you a list of short term rental friendly buildings to think about while you figure out financing.

Pretty respectable source’s research “found that short-term rentals are not the biggest contributor to high rents, especially when it comes to the most vulnerable segments of a city’s residents.”https://hbr.org/2024/02/what-does-banning-short-term-rentals...

Hey @Gerald Joyce - I am a sucker for utilizing as much space in my own Chicago buildings as I can....even if the numbers don't pencil out perfectly on the cash flow because like your Ravenwood building my buildings are in Bucktown and I know the long-term appreciation will far out way the short term cash flow...The question is, with your current situation can you bridge that short coming?

Even if you could discriminate and direct single mothers into the housing you would buy I predict in short order you would be evicting them, foreclosing upon them, or going bankrupt yourself. 

The short answer is they don't They are struggling with CFA, maccas, in n out, etc.Plus tons of healthy salad options and cheap Salad To Go.

Our plan is to subdivide and sell off lots to pay off the loan and keep the rest for to develop as short term rentals or an event venue.

I would say Short term rentals (air bnb), Mid term rentals (renting to nurses), Fix and flip, mini storage, commercial buildings.

If i were to airbnb it out for the last few weeks of December, would i be able to use the short term rental loophole to do bonus depreciation on the property (with a cost seg of course)?

I am pondering the idea of starting a short term rental management company.