Some folks have already given good advice, and I want to add a quick tip for how to get data on potential STR properties.

I had still kind of been contemplating further research on this program, but you talked me out of it.

I think I have all of my ducks in a row but I want to hear from other investors who are interested in this model.Any tips?

If this strategy interests you, research PadSplit for further insight.

These are good questions, but keep in mind that a month of obsessive research is still the absolute tip of the iceberg.

A 1031 exchange allows you to defer not only the capital gains tax but also the depreciation recapture tax, which can be at a higher rate.If you have any further questions or need assistance with your 1031 exchange, feel free to reach out!

This in a desirable town further North.

🎯Your QI should be:Independent from your transactionFree from conflicts of interestFocused solely on exchange servicesClear about their role limitationsPRO TIP: Per IRC §1031(k), your QI cannot be:Your agentYour attorneyYour CPAYour realtorYour relativewithin 2 years of the exchange!

Winterizing Your Home: Tips for Draft-Proof Windows and Doors" – Offer seasonal advice."

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).