Hi TMC,

I am doing this quick, so forgive, and remind if I miss something...

A boring machine with auger bit is the first choice, need is a brace and bit with auger bit, and third is a 40 mm (1 1/2) out canal gouge with a #5 to #9 sweep. You can move a lot of wood with a gouge. Most American Timberwrights don't do much gouge work, but I would be lost without mine as I do almost all my chisel work with gouges. Either sweep or "v's."

Best drill bits and all we use unless antique or custom:

http://www.woodowl.com/

Jim R. is the first place to go for antique/used then after that where he recommends. I use almost exclusively Japanese hand tools for my work, as I work in the Middle Eastern through Asian timber framing modalities and styles. I do like (love) some of the stuff coming out of Latvia for tools:

http://www.johnneeman.com/en/tools/chisels

For power tools it is a big mix up, but the core is makita, and festool.

I love "tulip poplar (magnolia)" and yes it is very much like white pine, just not as knotty and it will check on you if you do not kerf you beams (Asian habit again.)

So I can see from you drawings you are going oblique brace and the European style. I know it well as I apprentice with Old Order Amish, but don't work by choice anymore in that style except when restoring antique frames. I will also assume you are using "edge rule" layout, and not "scribe or line rule." I will leave it up to the others to make suggestions in general, and will speak up if I could add anything they don't. Design should be checked by PE.

Yes you are over thinking this...but that may be part of the fun for you.

Regards,

j