Transom rebuild in my future?

[Jswingle13]

Found this drip while I was topping off my gear lube. I am hopefull that I can run it some this season before I tear into again but I fear the worse. I recently patched up my speedo attachment holes that where leaking and thought I was good to go. I can put all my 230 lbs on my drive and there is no flexing. Please let me know what pics I can provide or what or how I can check this better to see if I can run or not. I read a little about taking core samples but there's not much room to get in there with a drill. Thanks for any input!