My belief is that in ordinary everyday conversation, the "t" is almost always audible. But it is usually a "flap t," not a "true t."
I believe that dictionaries are reliable authorities, so I'm about to check one. I feel quite sure that "plenty" with an audible "t" is the most frequent pronunciation. I will be surprised if "plenny" is listed as an additional pronunciation.
American Heritage and Merriam Webster show only one pronunciation, with a "t."
Therefore, I believe that "plenny" without a "t" sound is not a normal pronunciation, and that when it is heard, it is the result of slurred or sloppy diction.