I haven't tried it but I feel like you ought to be able to steal more if you update your steal skill.
Also I think stealing would be better if it was based somewhat on the persons view of you (I can't remember the exact terms right now) but there seems to both be a general suspicion level (bottom of the mini map) as well as individuals rating (I only can see this in the store view). If you are well liked you should be able to steal more because people aren't so worried about you being in the area but if you are not well liked then people will be more paranoid while you are around. If you are caught or strongly suspected of thievery then of course these numbers should go down.
The other thing I really wish was changed about this mechanic; there should be a timer after stealing. People can't stay extra paranoid forever. Eventually they ought to return to normal life.
