My old 67 Firebird had a 455 bored 0.060" over. I drove it from Houston to Dallas twice for the Pontiac Southern Nationals, and another time to Corpus Christi for a car club function. It would get to 190 on the highway, doing 70 or so (3.42 gears, 275/60-15 drag radials used all the time), but would actually run rather cool in traffic. It had a BeCool radiator, a Black Magic shrouded electric fan, and a CSR electric water pump.
At one time it had a 4-row copper, regular pump and a flex fan, and still never overheated. But it ran cooler (and a tenth quicker) with the electric fan & pump.
As Nas stated, just get custom pistons. NO NEED to bore from 0.040" to 0.060" if all you need is 0.047" (or whatever). I've bought a couple sets of custom pistons from RaceTec this year, and they assured me that they can provide the pistons at ANY diameter I desire. Their price (to me, at least, I have an account) is actually a bit less than some of the "off the shelf" pistons on the market.
Have your machinist determine the minimum over-bore needed to clean up the cylinders, and get pistons to match.
Even better with getting the custom pistons, they can tweak them to give you the EXACT compression ratio that you want, as well.