I work for a rather large (5m cases a year) wine company and barrels are our bread-and-butter. In terms of wine barrels - here's the quick and dirty:
Most oak is used for three years. The barrels are toasted to various specifications when new because it caramelizes the sugars in the wood and helps impart more tannin and oak flavor to the wine. After about 3 years, most of the tannin has been leeched out of the wood and the barrel is "retired". The first year is probably the harshest and extended time in the barrel can make the wine astringent and scratchy on the throat, but the increased tannin content in the resulting wine makes it more age-worthy. The second and third years, depending on how much they were used previously, are the sweet spots for many winemakers. Some wineries stretch the barrel use for 5 years or so but at that age its more of a storage vessel. After retirement, many of the barrels are given away or otherwise disposed of (turned into cheese trays or some other random thing sold in Williams-Sonoma for 9x what the whole used barrel is worth, etc.). Re coopering them is occasionally done, but often doesn’t make financial sense. Basically the barrel is taken completely apart and the interior is planed back to raw wood and re-charred. A re-coopered barrel is never the same quality, since the wine draws from pretty deep in the wood and even re-planeing it can't get to completely virgin oak.
As for brewing, you would really want to stay away from a young barrel since the tannin it imparts, while desirable in wine, clashes with beer, even barleywine.
If you're really interested in barrel aging some stuff and have some time, head up to nor cal wine country with a truck. Used barrels fall like rain around here. They're almost a nuisance. I just gave away the three I had in my back yard.
Anything specific you're wondering about?