I have entered the lottery since the forst year they have had it, and I have yet to be picked. I recently found out that I have better than 50/50 odds to be picked this year because each year you are not picked, you get an additional entry the following year.
I have been told by a friend that if you are selected you are given a contact info sheet whoich contains Western Maryland homeowners that have complained about nuisance bears and are more than willing to let you hunt.
So few bears are allowed to be taken (50 max) that it's really not hard to find someone who is happy to have you there.