When in doubt, ask an engineer. :)
Question 1: What’s the meaning of ‘the final roof undercoating of three-by-fives?’ ( final roof undercoating? )
The wood making up the final structural layer of the roof, was made of (probably wood) cut to three inches by five inches, by something long.
Example A four by two is a structural piece of wood 4 inches by 2 inches by however long you need it.
Question 2: What’s the meaning of ‘it might be nearly two feet through the center?’ ( its diameter might be nearly two feet? )
Yes, diameter, if you can define that for something irregular.
A measure form side to side, "thorugh the centre".
Question 3: Can I also say '‘the final roof undercoating of three-by-FIVE?’ If not, what's the difference between '‘the final roof undercoating of three-by-fives' AND '‘the final roof undercoating of three-by-FIVE?’
No, sorry.
inches, they are relatively small things, so it is made of many of them, plural. The total of many of them makes up the roof structure, as well as any structure below them.
.
That much clearer?