In my opinion, I like a cash asset, but they may be able to sell now, buy a smaller house for themselves, and a rental property or two in Texas.

With hopes to build two additional cabins in the future.

VRBO bookings in that 30-day window, I would then go live with my Airbnb listing, open out the calendar a little bit further so adequate availability shows, and take advantage of it’s first week or two?

However, I’m unsure about the utility of having two paid-off rentals 25 years from now.

That (and insurance issues) are two big risks.

These are two entirely different worlds that need two completely different skill sets to effectively manage.

It's down the street from our rental which we BRRRR'd two years ago.

About two weeks later, the appraisal came back with a value that was off by approximately 35%, leading the lender to reject the loan.I contacted the lender to explain why I believed the appraisal was flawed.

Two years ago, I had to deal with a 1,500ft townhome with a horrific cat odor.

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).