are you comparing a used 09 with a brand new 08?
there will be defender of both the 2nd gen and the first gen here my advice is to drive it yourself.
some say the 1st gen have better handling however I test out both when shopping for mine and I think the 09 is better, more refine.
exterior wise 1st gen does have a classic design that have withstand the test of time, 09 on the other hand is up to each person's interpretation. however buying a brand new car that has already have a new facelift is something i cannot do.
interior, 09 wins hands down.
option wise I do believe if you are going full option the 09 have a bit more toys compare to the 08, correct me though if i'm wrong.
than comes one crucial point, are you the modding type? if so the aftermarket support is non existent for the 2nd gen yet that might also be a thing to keep in mind.
which ever fx you go with, i'm sure you will be satisfield good luck on your search