Walkarounds make a great family boat, I 've been running one for 20+ years. Cuddy is great to store your gear. You can run a kicker with an I/O by tieing the the two motors together. I 've had both I/O and outboard, outboard allows for more cockpit space and I think is easier to service. If you are looking out of state be sure to watch for boats that have been in saltwater. I would suggest you decide on power choice and size before you lock in on brand. Important to have a vehicle big enough to move it around too. Have fun looking, should be some decent rides in your price range.