But, if a cost-seg study is done on the old property, you can manage Sec. 1245 recapture tax by doing a study on the new property to confirm it has as much or more Sec. 1245 property.You cannot swap a fully depreciated gas station for a raw piece of land and avoid recapture - you must replace all the 1245 and 1250 property.3) OZ - Sure you can defer your capital gains for a few years into an OZ fund, but the magic of OZ investments is the ability to achieve tax-exempt growth after a 10-year holding period.

The only thing I do manually is pay county taxes because the county we operate in uses some antiquated software that's incompatible with Hospitable.

We can do it Bevin, need to see the deal parameters to confirm.

If the math works, $750K could be solid, but confirm zoning, density, and build feasibility first.

I don't want to pay for another system or software that doesn't do what it say's it will do. 

You can propose your rent amount like you would with a regular tenant, but it has to fall within their payment standards for that zip code and unit size, and they’ll confirm it’s reasonable compared to other rentals nearby.

Because people can be a bit fickle at times, I'm worried that I will schedule an Open House and no shows up even after confirming that they were coming. 

My first self-developed software gave me efficiency.  

(Plus, the Big Creek Greenway is excellent for cycling)My background is in technology and data analytics, primarily in healthcare software.

Zoning & ADU ConsiderationsChicago’s ADU Ordinance applies if you create an additional dwelling unit beyond the existing count.If you stay at 2 units total (just shifting one unit partially to the basement), you likely don’t trigger ADU rules—but confirm with zoning since each ward can interpret things differently.If you want to eventually rent the basement as its own apartment, you will need proper zoning, permits, and a second exit per Chicago code.3.