Your dilemma is an easy one for me to answer.
-Once you have explored the entire Lake Erie, all of the other great lakes, there is nothing else to see or do, sell your condo, and buy the trailer and truck. I doubt anyone could do all of that exploring in a lifetime!
You could explore one of these other bodies of water in a weekend. (Inland lake or a certain pool on the Ohio river). Then, once you get bored of these places, (one week), head to the ocean.
That's what kills me, you can go to a small lake or the river, crack the throttle wide open, trim it up, and steer the boat with your pinkie toe until you reach the end of the lake or dam. What fun is that? Don't these guys like to "drive" their boats?
It sounds like you have a great setup, with the condo and everything.
Here is another suggestion, do what I did, and buy a small 18-20 foot tunnel hull with a big Merc hanging off the back of it to take to the inland puddles. You can tow one of those with a Yugo.