@AboveTheBest I totally forgot about this thread. Sorry man.
We have put in at Duffys Landing before in Jeffersonville. It's relatively safe. Same for Cox's Park off River Road in Louisville. Although not sure I would want to leave a vehicle there overnight. I would also consider the state park just outside Charlestown, IN. It's a LONG LONG drive back in there from highway 62, but once back in there, there aren't many people to be messing with stuff. I'm unsure if it's patrolled regularly or not, but it is a state park. They have a nice somewhat new ramp there.
Might be worth a call to Marine Sales and Service there in Louisville. They have a ramp, and their lot is gated/locked. I'm sure they would let you park there for a few days, use the ramp, and store the truck/boat for a small fee. That is probably the MOST secure you're going to get to be honest. In the Louisville Area anyway.
If you're going to be on the boat for a few days and truly don't need the truck/trailer. I'll be happy to pick them up, drive them home, and store them around the corner from me (within sight from the back deck) for a few days then put it back when you're ready. I'm ~15-20min from Duffy's Landing or Cox's Park and cross the bridge daily anyway for my commute.
I also have an Aunt with a house in Wesport that is a "vacation house" and she's not out there often. You can launch there in Wesport, drive over to her place to store the trailer, then walk down and use her dock to board the boat. It's still outside, but that is a relatively low crime area, so I would feel comfortable leaving a truck/trailer there for a few days. I can ask if you're interested.
Another thought is the small marina that used to be Heathers on the River in prospect. They have a boat "valet" service there for the small community residents that live there. I would possibly reach out to them about storing a truck/trailer inside the gates for a few days. Rose Island Yacht Club is the name of the place. See below (click or larger image).
I would say Madison is a bit more than an hour. We made the trip ONCE in our little Rinker 182. Want to say it was closer to 90min, but was still doable. You'll need fuel at either end to get back regardless of where you stop. I know the drive down from Westport to Downtown is about 45min at ~30mph. It's a good little cruise.
Let me know if you need more info on any of these places. I can dig some more
Also, let me know when you'll be in town, maybe we can have an impromptu "meet up" with
@sunbyrned as well?!?!