Since I originally posted this (thanks to the 1-2 day wait between first posts, something I really like about how this forum operates), I managed to beat the main issues I'd been having, particularly Monk Silver & Warlord Silver, but my ass has been consistently kicked by the likes of Rogue, Assassin, Sorcerer, Bloodmage, & Priest Silver.
With Rogue it's a problem of not being able to balance my tile usage and my ability to level up: either I waste a bunch of space, or I'm severely under-leveled for the boss. For Assassin, I think it's due to a reliance on a particular strategy (namely the Goblin Experience Junkie strategy) and an unawareness of any other optimal strategies for taking out the 3-part Anoobiss Boss battle, which I would very much appreciate. For Sorcerer, it's a problem of finding the right enemies to deal with, and constantly being pestered by the likes of the Stone Golems & the Animated Swords that haunt that level, as well as the final bosses Fireball retaliation. Bloodmage Silver is at least thematic, as I'm pretty sure extended play of that level could cause me to grip my temples so ferociously that I begin to cut deeply into them, so there's that, but otherwise, I have nary an idea of how to deal with it, which is also due to my general sucky play of Bloodmage. And finally, on Priest, I seem to be having a similar problem to my problem in Rogue.
I wish I could provide scores or videos to help, but right now my computer is on the fritz. Though I still love the feedback on simply my post - I totally didn't expect such a positive response! If anyone could provide extra help in the meantime before I can get my computer back in working condition, I would appreciate it greatly, and I would hope others with the same problems would, too!