STR inverstment near Chicago

[Madheshwaran R.]

Hi, I am a newbie trying to purchase an STR property and hoping to save on my taxes from my W2.

Could someone please help me understand what type of loan is best for my situation? I thought of getting a commercial loan or getting a loan through an LLC. However, a loan officer suggested getting a vacation home loan, then transferring the property to an LLC. If the interest rates come down, I can transfer the property back to my personal name, refinance, and then transfer the property again to an LLC or trust.

Second and most important thing, I would like to get an idea of what type of property to purchase that best suits for STR in Chicago area , near by states like WI or MI also I am fine as long as it is closed to Chicago.

[Jonathan Klemm]

Hi there @Madheshwaran R. - I have an STR here in Chicago and the only reason I keep the STR is because I have been grandfathered in since it's been over 5 years.

In all honesty, you are better off doing a long term rental then trying to mess with a short term property in Chicago these days.  It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.

The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.

I'd actually highly suggest Michigan because there is WAY LESS restrictions.