No discussion intended, no endorsement implied, but this outfit shows some custom painted WC cabooses: http://www.thebluecaboose.net/caboose10.html
We (WC) actually had a couple painted cabooses, I think they were bay window though. We parked one of them next to HWY 41 in North Fond Du Lac. I think there was one other. We also did a couple of Point ste Luc cabooses as remote cars but I don't remember what happened to them or if they got painted.
I think that WC bay window caboose is still parked along Hwy 41, just north of Fond du Lac. I'm driving up that way on Saturday (prepping for the EAA convention). I'll check.
The WC Photographic roster shows caboose # WC 11 through WC 19 and WC 104 that was the first page of 41, I didn't look at the rest. Here's one of them. www.rrpicturearchives.net/showPicture.aspx?id=609764 I have a Bluford shops undecorated long roof Transfer Caboose coming, think I'll fantasy this in WC
WC also painted an ex-CNW/CGW cupola caboose. The Atlas NE6 cupola caboose is close to the body style. It was painted at "DBR Shops" which is actually a siding just north of Milwaukee where it was kept for local use - I think someone was joking, but the lettering was on the caboose in hand painted gold lettering. There used to be maroon paint spilled on the ties from when it was painted. I don't have a pic handy right now.
Gimp, It is no longer along the freeway, although the foundation is. It has been moved to a park north of town and repainted into some kind of CN tribute scheme.