My experience with DNR reps at Monroe is they range from incompetent to clueless. You're giving them a lot of credit to tell you ahead of time exactly what size boat they will approve.
BTW - a completely different, and much more comfortable option would be to keep the 19 foot bowrider, buy a cheap condo at the pointe with a garage, sleep easy and launch the boat when you want to go out on the lake. It'd probably be cheaper in the long run also.
Ha... I know what you mean about the quality of info that sometimes is provided. I was able to speak with the person that actually sets the policy, so I will take what he told me as correct in this instance.
We actually thought about a condo at the Point... thing is, we already live in Bloomington about five minuets away from there, and quite frankly it is just not exciting enough at Monroe to justify buying a condo. Now if you could actually go somewhere while on the lake (like you can at Kentucky Lake or Cumberland) we might look into it. What makes Monroe nice (the lack of commercial building on and around the lake) also works against it as far as being an entertainment desitination. We look at it more as a getaway place that we can get to quickly vs. a place for a vacation (if that makes sense)
http://www.eaglepointe.com/Take a look at the Pointe listings here - they range from expensive, to dirt cheap.
http://www.connection-realestate.com/listings.html#