A home buyer wanting a bigger home is often simply referred to as a move up buyer. The best strategy for a move up buyer varies with time and with the locations of both the home being sold and the home being bought. Looking at the sales price vs. list price for homes in both areas lets you judge how easy it will be to sell your old home and how much competition there will be to buy your new home.
For example, the high number of houses sold in Palo Alto over list price around 2014 indicates it would probably be easy to sell a home there but there would be a lot of competition to buy a new home.
Please visit buying a home while selling to read about some real examples for move up buyers and others.