@Mehgan Moore
Hey Meghan,
I've heard of successful condo investors out there but I'd consider a few things - 1) HOA fees 2) Whether or not they allow short term rentals (airbnb, vrbo, etc) 3) whether or not they are prone to charge special assessments and 4) whether or not the HOA board is strict in regards to rehab.
I used to live in/own a condo in a high-rise building in a very popular area on the north side of Chicago, off of the lake, with trendy restaurants and bars nearby. Assessments were high for various reasons among them being we had a doorman working 24/7 and property management and handymen on premise.
The building was also very old so they were constantly raising the fees and slapping on special assessments. The previous owner before me had to pay a 25k special assessment to redo windows and siding on the building.
Despite all of this, I tried to make it work and decided to rehab the property and live in one room while renting out the other. During the rehab process, it was very difficult to get through it because property management would constantly send their handymen to check up on us and they would always point out something they wanted us to change. Some of the requests were reasonable but some were just ridiculous. It was almost like we were being micromanaged. There were many days where my contractor (aka my dad) would get in shouting matches with property management and the handymen.
Nevertheless, the rehab got done and we eventually rented out one of my rooms on airbnb only to find out 2 months later through a letter from the city that my building was on the short term rental prohibited buildings list. Therefore, I had to delist my room.
So, for all of these reasons, I sold my condo and bought a duplex to househack instead.
I hope this doesn’t discourage you from condo investing. But, just wanted to share my experience with you and encourage you to vet thoroughly the condo in which you invest in.
Hope this helps!