Like a calculator to simulate this strategy (https://www.biggerpockets.com/forums/61/topics/795487-retire...), maybe showing how much equity could be pulled out of which property when, whether the portfolio would still cash flow, etc.

Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

Personally, I do not like any strategy or approach that aims to benefit from the misfortune of others.

This will be the best platform to educate yourself on investment strategies.

., I left Anderson for a small firm that will do the actual taxes and then another company that specializes in tax strategy. 

You might consider other strategies, like taking a home equity loan or refinancing to fund repairs, but consulting with a tax professional or CPA would be the best next step for your specific situation. 

I am trying to calculate my returns over a 10-year period using the rent-by-room strategy, which results in significantly more cash flow than traditional rentals.

I have checked with our lender and keeping this home's mortgage will not effect qualifying for our next house.4.

Want to dive deeper into multi-state tax strategies for your portfolio?

Thanks @Robin Simon I plan on reproducing this strategy in 2025 to buy 3-5 more.