I’ve been trying to learn a lot about Airbnb and want to get into that side specifically.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Experienced managers can help evaluate potential investments by providing insights on rental demand, market rents, tenant preferences, and location-specific factors that affect leasing success.For example, rental properties need to be close to conveniences like major roads, shopping, and schools.

Specifically, what research results told you these were two good cities to invest in?  

In that case, you’d typically need to file a legal challenge, which could involve going to court and showing that the restriction is unnecessary or unreasonable.The best advice I can give would be to consult a real estate attorney to understand your specific situation and options.

They are a new international lender in Costa Rica offering 30 year, fixed rate mortgage loans specifically for American investors.

This protects against potential claims and liabilities specific to the rental.For tax purposes, maintain clear records of rental-related income and expenses, allowing deductions for insurance, utilities, maintenance, and depreciation proportionate to the rental unit.

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

Any advice is always appreciated.I have been BRRRR-ing in Milwaukee since 2008, if you look on my BP profile page you'll find a video.

When it comes to analyzing properties, I’ve developed a specific checklist to make sure the home fits both resident needs and operational goals:Square Footage: Ideally, at least 2,000 sq. ft. to ensure enough living space for residents and staff.No Stairs or Pools: It reduces liability and keeps the home accessible for everyone (this is just my preference).Corner Lots: I love corner lots because they often provide extra parking and outdoor space—both of which are critical for families and visitors.