I haven't slept all day, it was worth it. I've humbled myself, hooray!
Short analysis
Hard mode was not enabled until this encounter, due to how much XP you get during an entire run even with doing bosses only plus the pit. Killing all bosses in HM + getting to floor 19 would just end you up past LVL 4. But enabling HM until you start doing the pit would leave you at the right LVL, with only one or two tries to attempt it. Given how I tested this run twice, the dizzy clock always seems to always stop at least 2 statues, the minimum amount you need to survive to heal. But then again, having it happen twice in a row might just be intentional.
This attempt was done simply doing a normal LVL 2 run to beat Cruel King, getting floor 1-9 out the way for quick access to floor 10, and farming a certain amount of wolves or winged noobs to specifically have 67 XP. Wolves and or bears can give 3 XP while x2 winged noobs in a fight can give 2 XP. By having exactly 67 XP, you're allowed to have 4 total attempts at this, since every attempt forces you to clear 11-18 again and get 33 XP.
Back to gamba'ing I guess, siiighhhh.