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The idea behind that tool is to make sure the seal lip stays pointed toward the back. Not really needed. IF the lip rolls as you install the piston, it will be hard to turn. Correctly installed, the new seals and pistons will rotate in the bore without much effort. Lube them all well with brake fluid.
Check the cylinder bores for wear or rust or pitting. I'd hone them them make up your mind. I always hone them anyway. There is a similar sleeve for your crank if the snoot has lip seal wear. or use an offset timing ci=over seal. I don't think anyone can give you absolute suggestions without seeing your calipers.
Designer Imagines A Corvette That Looks More Like a Corvette Than the Corvette
Slideshow: A Jaguar designer's personal project imagines what a modern front-engined Corvette might look like if Chevrolet revisited the golden age of the Stingray.