1988 Pontiac Trans Am transmission issues

1.I realized that I have a leak coming from the transmission line that hooks to the bottom right side of the radiator.
2. Tranmission will not automatically shift into the last gear in regular drive, nor will it shift all the way out when I shift to overdrive. It seems like it's not fully engaged, and vibrates.
3. On cold start it takes approximately 3 to 6 seconds for the transmission to go into reverse. Going into drive no issue.

Hopefully, this is minor, as sometimes it works fine, then not. I look forward to hearing from you, and thanks. Jeff Morgan Donation to follow.