If you are just getting started here in Chicago, house hacking is the ideal situation.

In my situation if I’m earning $18,000 in cash flow from a property my tax benefits are offsetting at least that amount and I’m still paying $0 in taxes so the real estate scenario is attractive to me.

In this situation, is it better to get a property through regular means, look what is on the market (through realestate agent), or maybe go through a sheriff sale?

Consider defining clear roles, ownership percentages, and responsibilities upfront, and ensure you’re protected if the partnership doesn’t work out.Since you already own properties, it might be worth consulting a CPA who specializes in real estate for advice on tax strategies specific to your situation.

Considering doing a 75% cash out refinance > 30yr 7.45% interest rateIn what situations might the 50% Rule provide a misleading picture of a property's financial health, and when would relying solely on the DSCR potentially overlook important factors? 

@Rosmery ThenMy partner and I are in the same situation, just he has 20 years of construction and development experience.

There should be some financial advisors or real estate attorneys on here around your area who specializes in hospitality ventures and might provide valuable insights tailored to your situation.

Depending on the situation, a taxpayer could offset some of the passive losses with active income.

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

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