I don't know for sure, I admit beforehand, but I suspect that the convoy of the achievement is the one north-east of Pirate bane, I remember Lona talking to a merchant and immediately after being assulted by a group of 4 bandits who immediately slaugthered the poor guy so I'm pretty sure that one is the right convoy.
Probably because you are not naked, if you have any clothes on remove them, when you complete their quest you'll not need to be naked anymore.
Lona must be naked. When you first enter the village, you will get the option to say "yes or no" to taking off the clothes. You have to choose yes to take off the clothes. After that, always have Lona naked before going into the village. Otherwise, they'll attack.
Yes but mostly no. The yes is you don't really want to do that unless you're into ugly old lady
Alternatively you can try prostitution with the females in Victory Square, but I dunno if it's a bug or just crossdressing males.
There is a cute necromancer girl that Lona can take baths with and eventually sleep with (literally), which counts as a free inn stay.
It's probably to track achievement progress so you don't go doom mode at day 1 and then change back and go back to doom mode after 1 year. It seems you deserve to be ridiculed for assumedly giving up instead of just tracking it normally...
