20 items total so you’d have a maximum of 16 items removed. If you go daily after the advertised end of first round (tomorrow, 9pm uk time) then you need 15 days before someone is guaranteed naked. Could be sooner if we all vote for one person!
so, yes, daily is probably better. that would mean one naked and everyone else with hands covering) on 5 December. 20th if two days
Alternatively, top two each round lose an item and get their scores reset to zero. That might work better with the two days to vote approach. On that basis, first one naked and other four with hands (on the basis that everyone loses one item at a time in order) would be on 27 Nov (1 day) or 4 Dec (2 day).
yes, I’ve created a spreadsheet…