I don't know exactly what that whine is indicating about the bearing's health - it could mean one of the rollers is wiped or it could be warped or out of alignment. I do know that if it decides to finally fail it will do so spectacularly, and you're definitely going to lose a lot of hard parts in your transmission and probably damage it beyond economical repair.

I've seen other posters here quoting $1800-$2500 to rebuild a trans but it's going to vary wildly between dealerships/independent shops and it'll depend heavily on your local labour costs. For comparison a trans from Tasca Ford will run you $2,156 for the unit plus labour to install it. A combination of the Sure Cure kit, a master overhaul kit, and a new set of bearings will run you $550 plus labour to pull the trans, rebuild, and reinstall it.

 

Taking it in to a ford dealership on Friday to pinpoint exactly what it is, don't want to be blindly throwing money around lol. I'll keep updated.