I am a boat owner as well. I have a wakeboard boat though not a cruiser. If you are good at maintaining your own vehicle then learning to do your boat is not so bad. But major fixs will cost you $$$$$. Having a place to store it (inside if possible) is something to consider too. As some boats will hold there value if taken care of. I have seen tons of boat with ripped and torn seats from not being covered. If you just want something for the kids to have fun on just get a decent ski boat and take them tubing and wakeboarding.
You would also have to consider pulling it in and out of the water. Unless you have a slip rented or live directly on the water. I myself live on a lake and have a dock which makes life a lot easier when it starts to rain its ass off while you are out on the water.
Yep, a lot of people say that two day thingy, but I am not one of those. I love my boat and taking friends and family out is very enjoyable to me. Plus sending a kid hurling off a tube 8 ft in the air is freaking hilarious.
If you need more info pm me. I guess i could start a group on it like, watches or cars off topic.

Totally cant wait for summer now!!!!!!!!!!! Early morning sesh when no one else is out yet and nothing but glass for days!!!!

Same here! I have 2005 air ski natique team edition, we have her loaded down with full ballast and a extra 250 in the center and 150 in the bow. The wake is huge and you hardly even have to try to clear the wake and land in the flats!!!