The short answers to your two questions are NO and NO. I am not aware that Bob Bruneau ever used the IT 988 caboose on a regular basis for sleep overs. He had another better heated spot he favored.
The caboose could not be repainted in time for the IT meet in two weeks even at WARP SPEED as we saw in Star Trek. The fastest way would be to hire a contractor to sandblast and repaint it, and that might take well over a month. That work would be done after body repairs, restoring the roofwalks and ladders (fabrication) and other missing parts, etc. Then after painting, someone to do the artwork and add lettering. So you would be looking at several months, best case, if you had the $5K-10K in your pocket to hire out the work.
There are plans to operate the caboose on one or more trains during the meet, and some work has been done to lubricate journals and test the air brakes in a static test where it sits.
Bob Bruneau is a long time IRM member who has held several offices at IRM. He was the General Manager at the time of our move from the foundry yard at North Chicago to Union and was in large measure responsible for completing that move and the early development of our Campus at Union. For many, many years he led the way and his vision and long hours at IRM showed the way for many of our electric car restorations and progress. He chose to be on site at IRM four or more days every week, a luxury many of us could not afford. Not that he could afford it financially, but elected to set aside job and other world financial gain for the love of trains. Time and aging catch up with all of us, to where we cannot continue participation at IRM at the level we want or are able to do. So Bob has 'retired' in large measure from IRM. Thanks, Bob.
The Illinois Traction Society holds an annual convention and this year IRM is hosting it. There is an informal meet and greet Friday night, April 29, and activities all day Saturday at IRM. We hope to have a number of pieces operating, including the Bridge Car, the Alton Car, the Class B, and a three car orange train. A number of IT pieces in the collection will be on display outdoors, depending on weather conditions, for photos, etc.
If you Google Illinois Traction Society you can learn more of the details and schedule. Come on out, get your reservation and ticket from the ITS, and you will have a rare opportunity to see and ride the largest collection of preserved IT equipment anywhere.