I used the 255 pistons in my 250 many years ago and they worked well with some decking, but the flat top pushed the CR too high for iron heads and now they are getting harder to find.
Let me toss out one more piston option that may be viable, available, and cost effective.
The piston that may work out is the 1979-1990, 258 Jeep, KB Silvolite pn 2227. It has a 1.63" height, a 3.75" bore (.070" overbore), and a 21cc dish. The pin is larger, though, so you'll have to open up the small end of the rod from .912" to .931".
Depending on your chamber size you can get a zero deck height with only minor machining, end up with a manageable 8.5 to 9.5 CR, and still retain some quench area.
The downside is that this is probably the last overbore you'll be able to do on your engine unless you were willing to risk a .090" overbore.
Let me toss out one more piston option that may be viable, available, and cost effective.
The piston that may work out is the 1979-1990, 258 Jeep, KB Silvolite pn 2227. It has a 1.63" height, a 3.75" bore (.070" overbore), and a 21cc dish. The pin is larger, though, so you'll have to open up the small end of the rod from .912" to .931".
Depending on your chamber size you can get a zero deck height with only minor machining, end up with a manageable 8.5 to 9.5 CR, and still retain some quench area.
The downside is that this is probably the last overbore you'll be able to do on your engine unless you were willing to risk a .090" overbore.