Being furnished is also extra work, more things to break and be maintained.

Thanks in advance! 

My wife and I bought a condo in NYC in the fall of 2023.

Anyone who has participated in a bad investment understands this.

These items depreciate in value over time.

With 40k cash, a wife that loves your current home, and 2 kids, stay put unless you can find a compelling reason to convince your wife to do another live in flip or live in a 2-4 unit house hack.

The area you are in is very good for appreciation.

We have equity in 4 of the 6 properties  ( really 5 one Mobile Home on 2 acres paid for no one will lend  ).

Sure, if you have an actual guest -- like your mother -- visiting and she breaks her leg and tries to sue you, then a regular homeowner's policy would cover that, but not if that guest were part of a rental transaction.

Your cleaners can make or break your business, and price isn't the only consideration.