Rule of thumb: don't shoplift if you want to stay on friendly terms with the merchants. Pickpocketing they don't remember (if you don't get caught, that is) but shoplifting they do. Also, if your PP level is as low as you said earlier, I wouldn't try but 1 PP at a time and then leave and Quicksave and then go back in and try again.
2nd: when Anna starts responding with the 'aliens' remark, are you able to enter talk mode with her or does it automatically kick you out? If it does then you are screwed. If it doesnt then you can always try to appease her with the item/gold.
3rd: If she takes the gold but says 'not enough' then I'd try reloading and dialing in a higher amount so you can get some idea of how much you'll have to sacrifice to appease her. It might be a better idea to hold off on appeasing her for now and come back when you've got the gold to spare. Also -keep an eye out for an item called a "Filcher's Band" since it raises your PP by +10 or 15. I kept 2 of them in my inventory for my bard to wear whenever we encountered an NPC and it made my life a lot easier.
