What areas in Chicago and Suburbs there is a demand for Midterm Rentals?

[Yanaki Bitsin]

Hello everyone I'm new to real estate and trying to learn as much as I can. Right now, I'm working on getting pre-approved to buy a property and want to make the best decision in terms of optionality (exit strategies). Right now, I have come to the conclusion from everything that I have consumed so far on the internet that STR and MTR strategies are the best in terms of ROI and producing cashflow. So I do want to eventually get involved with it, but because my credit isn't great and my starting capital isn't much (less than 10k), I can probably qualify to buy something under $200k, so I'm thinking about buying something for myself as FTHB to live in and then having the option to rent it out, ideally as a mix of STR and MTR, but I would be happy if I could just do the MTR. My questions are:

1. how can I check with the HOA that I have the option to rent it out as MTR or STR?

2. and in terms of location, how can I research which areas have demand and the gap?

[Bonnie Low]

If you're looking to buy in a homeowner's association they all publish bylaws that will state what their rules and restrictions are. You can probably find them online. If you do go forward to buy within an HOA, take the time to go to a few of their meetings or at least read the minutes of their meeting to see if there's any discussion about STRs or MTRs. You want to know how they view them. Are they discussing them in a derogatory manner or are they clearly supportive? You wan to gauge the climate of the HOA. And that climate can change over time.