It is a 2000 model and was taken off 4 months ago for a total paint redo. When re-installing it, do I need to replace the big seal that seals against the outside of the transom? It appears like the seal is in good shape. I am not being cheap, I just know that sometimes getting a new seal to seal (and get seated properly) can be challenging also.
Thanks!

Yes put on a new seal. You have gone to a lot of work to get the boat this for.
Mac