Also, here's a great article that describes the REPS status:https://www.aicpa-cima.com/resources/article/tax-rules-for-r...And another for the passive activity loss limitation that other mentioned:https://www.irs.gov/publications/p925

Learning how to use the correct tools and materials for a job, YouTube videos and even ChatGPT will help you get through 80% of the problems you will run into.My rule was I would not mess with HVAC, plumbing and electrical Or if it would take more than a few hours. 

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

The general rule of thumb when using debt is to ensure that whatever asset you buy with the debt should make more than the debt service.  

Each area has its own rules on how it works, but basically, you buy the house, pay a deposit and agree to rehab the house within a certain amount of time.

When it comes to housing, the FHA rules apply in addition to those of your state/city.

Here are some key elements to include:Lease Agreements: Ensure your contracts reflect the latest laws, such as notice periods for entry or rules around security deposits.Fair Housing Compliance: Familiarize yourself with federal, state, and local fair housing laws to avoid discriminatory practices.Property Standards: Regularly inspect your properties to ensure they meet safety and habitability standards.Tax Documentation: Keep accurate records to comply with tax reporting requirements.4.

With this one I would a paragraph that states " in case of any unforeseen circumstances due to the plumbing, we ask that you not flush wipes or pour grease down the drains "  that way you have stated that in the rules part of the listing.  

In a very loose rule-of-thumb estimate, your Net Income (revenue minus expense) may be about 50~60% of the gross revenue. 

Hey @Joel Oh, so let's clarify the NYC rules around STRs.STRs are legal in NYC as long as these directions are followed."