Don't do it.............. Boats beat cars hands down in terms of time investment. Money investment is probably a toss-up.
Been there done that- grew up with boats 'til dad had health problems in mid 80's. Big time & money investment and you have to be on the water/away from primary home to use it. At least with the race/track cars, you can tinker with them at home. With boats, gotta be on the water to work on them for the most part. Never really understood the Chicago marina gig. Lake is frequently too rough for the small pleasure boats and I always thought it was lame when people had boats that never left the marina!
Grew up with a number of different boats:
Mid-1970s = 20 ft. Cruisers Inc., then a 22 ft. Bayliner
Late 1970's to early 80's = 1979? 35 ft. Kingscraft houseboat- riveted aluminum can with a crappy Chrysler V8 (single) but one durable sucker! Man did dad upgrade that- added a flybridge, made cabin out of the front lower galley storage area, refurbished the entire interior. He loved that stuff.
Early 80's to 1985 = upgraded to 1972 43 ft. Nautaline houseboat w/twin Ford 302's & flybridge. Nice boat back in the day. Bought it from an airline pilot who spared no expense maintaining and upgrading it. Dad loved that thing. Finally acquired his target, a nice size twin engine (inboard) houseboat. Then dad's health issues put an end to it for us. It was good while it lasted though!
In between the houseboats we had a 16' Mark Twain runabout ski boat and then upgraded to a 1975 19 ft. Century. The Century rocked- 225 horse 302 with open exhaust. Back then, we thought we were pretty bad a$$ doing 50mph with the "Red Baron" hotrod boat. Well, until the rich punks with their Glastron jet boats would blow us out of the water!
Dad was a diehard boater- lived, breathed and died boats. Whole family life revolved around boat routine, which was as soon as the midwest winter breaks (sorta) in March/April you're at the marina every weekend until winter returns- late Oct. early November. So that blew the whole childhood/youth athletic oppotunity for me and my brother. Am I bitter? Nah. It may have deterred my social opportunities at home as a kid, but little did I know I lived the good life for a lot of years- got to drive (unsupervised) the ski boats all over the river at 11 yrs. old. Learned how to "drive" long before other kids even remotely were ready to take the wheel of large, dangerous, fast machines!
At the time I didn't wholly appreciate what a great hobby my dad instilled on the family. Looking back I had it pretty good as a pre-teen. We were living the good life hanging out at Ottawa/Starved Rock marina & river area every weekend, rain or shine.
Point being is I am biased because i've been there done that. Talk of boats nowadays from the wife results in a "no @#$%ing way baby" from me. Already been thru that phase of my life long ago. Even as a kid I could see all the work it took to do it hardcore like mom & dad did. I'm not willing to put in that kind of effort. I asked my older brother (i'm 37, he'll be 40 soon) about his boat perspective in terms of whether he had any desire to get one. We share the same feelings- no desire on account of we got it out of our system when we were young I suppose? Well, my perspective is also biased on account of i'm already WAY immersed in the Porcha hobby!
Good luck dude!!!