I would suggest doing them about ten versions at a time. Go for 162, then 172, and so on. The big sequential release page is here:
https://github.com/hydrusnetwork/hydrus/releases
I think it goes back to v130 or so. Trying to do thirty eight updates in one go is probably too much of a step because of bit rot. But you can try it, if you like! I suggest you back up first.
Be aware that the v185->v186 step requires a 'clean install', as detailed here:
http://8ch.net/hydrus/res/1589.html
Essentially you have to delete everything except your db folder when you update that step, to clear out old files that are no longer valid. This is probably the cause of the weird error in >>1793 . The 64-bit v190 exe is likely trying to load some old surplus 32-bit dlls and having a problem. Since your install dir now has some 64-bit dlls, attempting to install < v186 also probably needs a clean install!
So, I suggest you delete everything except your db folder right now, to clean things out. Make sure you have that db folder backed up if you have enough spare hard disk space somewhere. This is important to do if you can, because if everything goes wrong and your db gets broken, it lets you try again.
Once you are ready, create a completely fresh install of v162 with your db folder and see if it boots, if so, then try updating to v172, v182, v185, [clean install] v186, v190. If one jump fails, let's say v172->v182, you can try v177 or a smaller increment. If a single-step increment doesn't work, then post the error here and I'll see if I can figure it out.