I want to thank everyone for their very useful advice. I have gone to check out some of the condos sent to me through the mls and so far, the seller's realtor has confirmed the HOAs of these visited properties allow rentals with certain conditions such as they only allow minimum 1 year leases.
The specific condo I'm looking at hasn't had a special assessment in something like 20 years since they have a couple million in reserves. They only allow leases for a minimum of a year. It's not a big cash flow property and I'm mostly looking at appreciation to add to my portfolio. I'll either break even or maybe $100 a month.
I currently have a 2 unit multifamily building that I purchased using my VA loan that I was house hacking but now have filled with two tenants and it does cashflow about $1000 a month. I'm hoping to eventually refinance into a conventional loan and use my VA loan again for a 4 unit building. I'm hesitant to do that right now since I have it at 3.25%.
I think I'll start looking up the different HOAs in Chicago and look up their bylaws.
