I might be a little late to comment on this thread, but I brewed something similar to this about a year ago. I took AHS's Oaked Porter and added some Maker's to it. I essentially brewed the kit as per the directions. I took the oak chips that came with the kit, soaked them in a pint glass full of Maker's for about 2 weeks (during my primary essentially). Then I put the beer in secondary, and poured the oak chips and bourbon right in. I let that sit for maybe another month and bottled.
My results were a very smooth beer, with a great taste. Early on I really tasted the bourbon, but it seemed to mellow out over time. I had one of the last bottles about a month ago and the oak tastes seems to really be there now, with less of the bourbon. It's still a REALLY smooth beer, and turned out to be one of the favorites of all of my beer (and bourbon) snob friends. They still talk about it to this day, which they don't do about most of the rest of my brews.
I decided to take another shot at this soon. In November I brewed AHS's Our Special Holiday Ale and it turned out great. For xmas, my sister ended up getting me the same kit. It takes me a few months to kick a keg in my place, so I decided to to tweak the kit a bit this time. I'm going to brew it as per directions, plus a few lbs of dme. Like the Oaked Porter, I'm going to let it ferment itself, then when it's done I'm going to add oak chips again, which I will have soaked in bourbon again. I also decided to add 2-3 vanilla beans (also in the bourbon soak). The Holiday Ale comes with a spice pack which I won't use (it gives a complex gingerbread cookie taste, which I'm not looking for in a bourbon beer). I'm probably going to let this age a bit longer than last time.
I highly recommend trying this, especially if you're a bourbon drinker. I would suggest a wee heavy, porter, or stout though - MAYBE a brown.
I got my idea for this from a brewery in Kentucky. My friend brought home a few of these and shared them with me and I thought they were fantastic!
http://www.kentuckyale.com/beer/Pages/KentuckyBourbonBarrelAle.aspx
Another good one that is similar is Bourbon County from Goose Island. I can find this a lot easier than the Kentucky brew. They are both sipping beers, and both are fantastic.
Good Luck!