Hotrodding a stovebolt is sort of like putting lipstick on a pig- - - -unless you've got a deep enough pocket to make some radical (translation" E$$$$PENSIVE) major modifications. There's no real advantage to boring the cylinders out more than what's needed to take the taper wear out of the cylinders. Radical camshaft profiles only add a measurable amount of power at RPM ranges that are seldom seen on the street. It's also necessary to increase the compression to benefit from the kind of power a radical cam provides. At low to midrange RPM, a cam with a lumpy idle actually reduces the power available for street driving and causes major losses of gas mileage in the process. The primary purpose of the mods your "machinist" is suggesting is to increase his cashflow at your expense.
A conservative stock rebuild would be a much better choice unless you have some kind of racing in mind, even if you have to go looking for a different shop. I spent a lot of years building all-out racing engines for round track cars and truck pulls- - - -it's always more fun to go racing on the other guy's money. People were willing to pay me well for engines that won races, and I could have fun doing it without bankrupting myself. Doing race engine stuff on a street machine is stupid squared!
Jerry