Real Estate Order of Operations

[Vidal Anguiano]

Hi all, Happy New Year!

I am hoping to get some advice from you all on my current situation. I currently own a 2BD 2BA condo which I was house hacking during grad school. I rented out the second room up until a year after I graduated, but now prefer to keep the space to myself. My initial thought with buying this condo was that I could house hack it while in graduate school and rent it easily (it's located near University of Chicago) once I moved away. However, since I own this condo in a building where 3 of 8 units are already renting, I could face considerable trouble renting it out with association rental caps. The option I am now considering is selling it.

Whether I sell it or not, I am now targeting my next home hack deal, whether it's a du/tri/quad-plex. Assuming I do sell, does anyone have advice on the order of operations when it comes to selling/buying and when I should be executing on relevant selling/buying activities? What pros/cons should I be considering when deciding whether to do one vs the other first or at the same time?

Thank you in advance!