During one sleepless night I didn't felt like playing or reading, and staring at my ceiling isn't as fun as it was - I studied it well during early "quarantine" back in 2020, so I wrote a small script. It parses given "dictionary", searches for words where last letters of one word are first letters of another, and then it merges them into one. As base words I picked classes from (A)DnD. So, here are the results:
druidiosyncrasy
magenda
clericochet & barnacleric
fighterritory
rangeranium & carnivoranger
barbarianthine & cinnabarbarian
cardamonk & monkaparinga
warlocksmith & talwarlock
toolbard & bardennes
wizardent
microsensorceror & sorcerorschach
municipaladin & paladinghy
roguest & twarogue

Of course, there were far more of those, some are much derpier that those here, but I think these are most "suitable" without me getting banned. I hope.
I don't plan to update script, in fact, I haven't even saved it, though probably it's not that difficult to recreate it, in case someone would like to keep up.