Chicago Downtown Condo for STR/VRBO/Airbnb - Bad Idea?

[Adarsh Sahni]

Hello all!

I am a complete newbie to this field (and forum) so please go easy on me. Me and one of my friends are thinking of buying a lakefront Condo in downtown Chicago (2BA/1.5+ Bath). We both live few hours drive from Chicago. Our plan is to hire a full service property manager to manage the renting out and maintenance part and use it for personal use few times a year.

We both are very busy with our daily jobs and cant really do the management and maintenance ourselves. We are realistic and goal is not to generate a huge income but to diversify our investment, use the business to lower our tax burden (since we both are employed and get hit by significant taxes at the end of the year) and make enough that it pays off the mortgage/taxes (or at least a major portion of it). Also, we want to buy something we see ourselves renting out on vacation.

Am I being unrealistic or stupid? Any advice would be hugely appreciated. Thanks!