Let's imagine a situation where you found yourself in this game world. What would you do, and if you had the chance, which giantess would you choose to end up with? That's a question for everyone.
Pfft, obivously go to Thalenor, just to learn what liquid uranium tastes like.
Jokes aside:
1) Strongly depends on where will I initially get to, but if I have no plot armor then probably just die, and not on my own volition. If I do have one however, then go to the most advanced society, which is Timfalme, and try to become its functional member.
2) Probably someone from Timfalme, but definitely not Orphelith, because it's too dangerous to be a weak yet important person of the biggest kingdom around. Not Croixelle either, just to not be dumped when she gets tired of playing secret romance with me. Probably not Margarita or Kive, because I don't need any actual relations and don't want to spend the rest of my life working under the sun the whole day. So if it's an option, then just the castle in general, if I am guaranteed to get a job and live there forever.