Quote from @Paul Sanders: Thought it might be interesting to post an update on this situation.In August of this year, a special meeting was called to discuss updating the bylaws or rules to disallow STR's in the HOA by the board as the HOA's attorneys agreed the CC&R's are ambiguous as to explicitly not allowing STR's. 

They at least finished my rehab and got the refinance done, but they place went untouched for 4 months after I purchased it, when they had explicitly told me that the rehab was underway. 

Quote from @Brendan Winans: I Made My Largest Single Profit to Date: $250K in 12 Months on a FourplexEarlier this year, I closed out a value-add fourplex that generated a $250K profit in just over 12 months.

Seller financing is another one - great option in theory, but modeling those scenarios takes forever so I only do it when the seller explicitly mentions it.I'm betting I'm leaving money on the table by not exploring every financing angle, but there's only so many hours in the day.

Many investors start with single-family because it’s a great way to learn the ropes, build equity, and get comfortable with the process before scaling into multi-family.

I am thinking about selling my portfolio of single family homes. 

I do think Multifamily certainly has advantages over single family, but single family has advantages as well.

You might find a single-family in a better area than a multi at the top end of your range, which could help with long-term appreciation and tenant quality.

As many of you know, finding a condo building that permits short-term rentals in Chicago is extremely challenging due to HOA and city restrictions.I just pulled data on a handful of active condo listings where the buildings explicitly allow short-term/Airbnb rentals.

But single-family homes can still compete if land value is low or outdoor improvements are high.Bottom line — it’s not “condo vs. home,” it’s after-tax cash flow vs. headaches.