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!

[Michael K.]

@Vidal Anguiano

Have a lot of questions about your situation but I will start with the most obvious one. Do you need the money from the sale of your condo to be able to get your next property? Or do you already have a second down payment saved up?

Trying to buy and sell at the same time is not a great situation to be in, you will be less appealing to sellers and may be forced to sell your condo for less than it's worth, avoid it if you can.