Felix, it's not that 4 is better than 5 and then case closed. It's a little more involved. I'm not entirely sure how the DamageBoost entry works other than that it "boosts" damage by the amount specified, especially when combined with autoleveled items. I.e., items for which there is NOT a specific entry in the data files but one which is generated from a base entry extrapolated to the crafter's level.
In other words, certain items seem "targeted" for appearing in certain parts of the game. Part1 - Part20 or something like that. The crafted weapons are the exception. They can be created in any part of the game given sufficient blacksmithing skill. Even at level 1. But if you make a WPN_Crafted2HSword_05 at level 1 it's not going to do NEAR as much damage as one you make at level 21. I hope that much is clear.
So it is very likely that the DamageBoost entry is simply the game's way of figuring out that, if we want a certain weapon that does a certain base damage to start appearing in the game (inventories of merchants, drops from mobs, contents of chests, etc.) at a certain time (i.e., when the player is around a certain level) we may need to adjust the extrapolated base damage of the weapon by an amount to get it around the right damage for that level of player. My limited experiments with DamageBoost seem to bear this out. Weapons I modified by taking out the entry entirely did increasingly crazy amounts of damage the higher the level I crafted them at. The "boost" (so quoted because it's really a reduction in most cases) seems to keep things in line. In fact the higher the base damage of the weapon the bigger the reduction seemed to be.
All that to say this: when you're able to craft a WPN_Crafted2HSword_04 (at blacksmithing 4), your level is probably going to be less than it is when you're finally able to craft a WPN_Crafted2HSword_05 at blacksmithing 5. So while the game actually reduces the damage of the #5 sword by 5% more than the #4 sword, the #5 damage should still be more by the time you're able to make it.
Now of course you could equip/unequip some gear that lets you make both at the same level. In those cases I would expect that the #4 swords are going to do more damage than the #5 swords unless you proc a #5 sword with the Large Damage Mod boost (seemingly a 50% chance). But if you don't get the Damage you're getting the Strength boost so what would you rather have, a sword that does 5% more damage or a sword that gives +1/+2 strength?
But on to your test. Pardon me if I'm assuming too much, but it sounds like your "test" consisted of making 2 swords? One with blacksmithing 5 and one with blacksmithing 4?
Since the blacksmithing 5 produces two types of swords randomly you really need to do more than craft 1 sword at blacksmithing 5 and compare the damage of the ones you get with +str and the ones that don't have +str but should have +dmg.
Also, you mention that the "Sharpening wheel did not improve the damage on the first ..." but before that you mention that it had 236-381 damage "... after sharpening ...." This is contradictory.
What I would do is get my bs to 4. Craft 3-4 2H swords. See if they vary. They should all be exactly the same damage and look. Write down their damage BEFORE and AFTER using the wheel.
Next get your bs to 5. Craft enough 2H swords to get some with +str and some without. Write down the damage of the ones with +str and the ones without (should be more). Compare their looks. The ones with +str should all do the same damage, and the ones without +str should all do the same damage. Sharpen and compare.
Theoretically the max damage of the bs 4 swords should be 5% more than the +str bs 5 swords.
Heh heh. If you're able to try all of the above and things still are confusing then by golly I'll make time to figure this out because I, like you, hate inconsistencies! (also like you I hate the "prissy" look of Flamberges - Real Men (tm) don't use such things! if I wanted curves I'd get me a woman! har har)

Good luck Felix!