I live in Louisville. I've actually rollerbladed from my house in the Churchill Downs area downtown then up Bardstown Rd. to the Sullivan part by Gardener Lane. I looked up his name online and saw some youtube video that featured him skating at the Louisville Skatepark so he could make a 3 mile walk so that might not be too suspicious. I used to walk my dog up and down Bardstown Rd. and Baxter Avenue nightly. It's a very popular area. People are there at all different hours and gets the most foot traffic in the Louisville area especially from college aged and teenage people like me. There is at least one 24 hour hangout at Bonnycastle Avenue and Bardstown Road. It is a hookah bar and restaurant. The area he was last seen is closer to the main bar section from where Baxter meets Bardstown and further down Baxter. There are usually huge crowds in that area, but also there are several popular restaurants and bars people hang out at near Lucia. I might go there with my fiance and dog. Maybe I could take pictures to give an idea of the area. It's one of the safest areas in my opinion because there is a large concentration of police and frequent police cruising up and down the road. I was mugged there once at 3am when I was walking alone farther up the road but for the most part you don't hear of that much crime in that area.
There's a large park (actually 2 next to each other) nearby that I'm wondering if they will search. There is also a very huge cemetery nearby called Cave Hill that some kids will climb the fence after dark to see the crematorium I think. If he was a skateboarder like the video I found then he may have gone to the skatepark. It's open 24 hours but is a sketchier area. It's by the Waterfront Park downtown. I had to literally help a 17 year old boy earlier this year because he begged to get in my car. A large mob of boys were following him and had tried to jump him already. They chased him from the skatepark to Main Street where I was at. I ended up getting out of my car and chewing them out and telling them they were immature and acting like Jr. highers and it's wussy to jump someone and shows cowardice. I figured an attractive 22 year old could humiliate them away lol. So I definitely could see being jumped a possibility here. With guys it seems like you can just randomly be targeted to be jumped in this city.