YOU Need to consider the lakes you will visit and what your goals are. For now it seems like the Outback will work for you. If the lakes or rivers you will run are on the smaller side this is also pointing you towards the outback. We live on a smaller lake, don't trailer, and have other boats to use. As well as being a hard core skier my kids are small enough to do anything behind the outback.

If however you are going to be on bigger waters, your kids are getting to be teens and want to be the next big air champs of the lake, and your not really hard core anything just want to recreate than consider the V Drive.