No updates in a long time, but I havent had the chance to ride the bike until today, and even then I only rode it for about a minute around my block. Here is the good, the bad, and the ugly.
The good is the rattling sound is gone, the engine sounds great, and pulls strong. The clutch is now working properly, no dragging, and neutral is easy to find with the engine on and off, no more sticking when shifting 1-2 and 2-1. The sealed head bolt did not leak, but I'll have to give it a longer ride to be truly sure.
The bad is 10 seconds into the ride I heard a vibrating nose that immediately amplified. This time it was easy to discover - I have replaced my timing inspection port plug with the DRZ plug, for ease if removal in the future as it uses a 10mm allen bolt vs a long flat slot on the stock plug. Turns out the new plug did not come with a gasket, and I forgot to swap in the old one, so the plug immediately loosened up. Very easy fix.

Here comes to ugly. I took off the plug to swap in the gasket, and keep in mind the plug is brand new with only 2 laps around my block. I looked inside the plug and there was a ton of metal shavings in it, and some shavings inside the port hole. I cleaned the shavings, took the bike for one more lap around the block, removed the plug and there were more shavings, but this time a lot less than the first time. I inspected the old plug, and there were no shavings in it whatsoever. There was no shavings inside the port hole when I removed the plug to set the engine to the TDC. Also, when I drained the oil to work on my clutch, I did not see any shavings in it either, therefore these are new shavings that got there within the 1 minute that I was riding the bike around my blocks.
The shavings are probably from me redrilling the head bolt that goes through an oil passage - and therefore I probably deserve what's coming for not taking the advice to do it the right way. I thought I blew most of them out, but I guess not. I'm very surprised how fast they made all over the engine, I imagine if I found them in the port hole, they are probably all over the engine as well. I'm also surprised that these shavings seemed to be dry, not covered in oil - almost if they got blown in there by air. Could they have got there when I was blowing them out with compressed air through the head bolt hole?
That being said, I will keep removing and inspecting the port plug during for the foreseeable future. Would it be a good idea to do a few oil changes with some cheaper oil ever 50 miles or so to try and get the shavings out?