You will need to check the bending planes that produce the thickest plate so you will check at least 2 in your example sketch and more if you want. The one you call tangential should probably be at 45° to the plate edge to give the shortest bend line. If the tube is square and the 4 bolts are square and the plate is square, the 45° line will be correct. Even if the tube is rectangular and the bolt pattern is also rectangular, the 45° line is the one I check.
Your PLS-POLE reference is more for 8, 12, or 16 sided T-Line poles where they consider bending only along a flat and not tangent to a vertex. Their equations come from ASCE 48-2011.
From ASCE 113 section 6.8 (I wrote some of it about numbers of bolts and the plate thickness, but was talking about big dead end poles with 20 to 48 bolts). Look at Figure 6-1a and check the bend lines 1-1, 2-2, and 3-3. If the hole in the plate is the same size as the HSS tube, you have to subtract the tube width from the effective bend lines 1-1 and 2-2. Choose the maximum bolt load for 3-3 and do the thickness calculation for all bend lines and pick the thickest plate.
There is a paper by a guy named Horn about pole baseplate design that is around 100 pages. Do a search for Daniel Horn and a paper called Technical Manual monopole bases. I found a copy at
that you can download. I believe he was in the telecom world and did large monopole base plates but the concept is the same.
Good luck.
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