Sometimes the most expensive boat is a free one. Also, depending on the capacity of your wallet, it can break you. Don't forget about all the cost associated with a larger boat. Haul outs, winter storage, slip/marina fee, larger insurance, maintenance that you just won't be able to do efficiently. A couple of years ago, we bought a 25 foot trailerable for MY youngest and I to bond over. Sleeps 5. Sails well enough for me. Cost us $2200 plus $1500 for a trailer. My wife and I can step the mast, and launch in 25 minutes. From my limited perspective, maybe something a little smaller? But I am biased. Whatever you do, I'm sure you'll have a great time!