When looking at the architect's plans, the new en suite master bathroom will be 8x12.

Hi @Nancy Cho happy to connect and talk business.

https://www.singlekey.com/en-us/ - I believe they screen the tenant as part of their underwriting before issuing the rent guarantee policy and the tenant also pays the premiums. 

@Rebecca Cho I’m going to be a heretic here.  

Buying a large new build home can also work well as a house hack as you can charge a premium rent, and generally most bedrooms built now a days have en suites (at least in my market).  

The HELOC would act as en emergency way to tap into their equity if needed - as long as they don't spend it unwisely!

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

@Aaron Frances - here is the processhttps://www.chicago.gov/city/en/depts/bldgs/supp_info/certificate-of-occupancy.html

Here's an example: https://www.schlage.com/en/home/products/JDE265SUTFFFSTR.htm...

Here's their page called My Lodge Tax, for STRs. https://www.avalara.com/mylodgetax/en/index.html Process returns, Save time and hassle.