As for the Countess of Leyawiin, nothing will happen to her if you don't do something dumb, like get her killed (or YOU being the killer). My advice, don't go on a killing spree while you are in towns. Keep your weapons in your inventory, not out in your hand and swinging like a lunatic. Nothing will happen if you don't go causing trouble.

For a lot of these, the solution is simple. Just get Sneak 100 (for all bonuses and 100% pickpocket) and Illusion at a 100 so you can create Chameleon spell 100% for 60 seconds (make sure you have high Intelligence stat for magicka pool because the spell costs 250ish magicka to cast), and you will be completely invisible. Make noise, pick locks in front of people, steal stuff in lighted rooms and with people present, and so long as you stayed crouched while the spell is active, you won't break stealth at all. So no worries about being expelled from a guild for stealing. They can't kick you out if they can't see you.

It's OP's Profile Pic.

The deep looks cute in the picture