IFR - You certainly have a strange situation, I still can't picture the details. Anyway, a few thoughts...
The allowable values for designing with wood are set well below its maximum strength. This is because of the huge variability in how trees grow & and the non-linear performance of (heavily) loaded wooden members. Even the maximum strength, Modulus of Rupture (measured in psi), is a generalized number. For example, here are some values for seasoned Douglas Fir:
Maximum Allowable Bending Stress: 900 psi (from reference document in my previous post)
Modulus of Rupture: 12,700 psi (from this link
)
This logic applies to all the engineering properties of wood.
For the issues on bearing, perhaps this reference, "Wood Structural Design Data" will provide more insight. Look at Page 40, in "Chapter 2A - Wood Beams". Here is a link to the free .pdf download
As for how to analyse your situation, I would start with the simplest assumption, i.e.
The 2x6 has a full length, uniform crossection of 5 1/2" x 15/16" (1 1/2" true dimension - 9/16" hole diameter)
See what the numbers tell you to determine if you need to "dig deeper".
Designing new structures with wood is well defined by NDS requirements. But figuring out what is acceptable and what is not for an existing application is still as much "art" as it is "science".
Best Wishes