advice: buy 1 nice updated house? Or 2 smaller properties?

[Maria Ferre]

Hi all, need some advice. 

I have an apartment in NY which I'm renting out and soon moving to the Norwalk Connecticut area with my small daughter. I have enough money to buy a 2 bed condo for about $300K in Norwalk, and then a vacation house in upstate Connecticut for another $300K which I can use, and AIRBNB.. I'd put $100K cash down on each property.). The condo would be for about 2-3 years of living until my daughter is old enough for school. 

The condo eventually will need a new kitchen, but not now. It's definitely do-able. I can rent if out if I move at some point. 

OR -- I can just spend $600K (200K$ cash down) on a totally updated, 4 bedroom house in a residential area of  Norwalk where my daughter and I can live. 

I want to put my cash in real estate obviously and wondering if it's wiser to split it up into 2 properties, or 1...