Hope I understood your first post right, here is my 2cents.
Silicone just doesn't work well for sealing the outside of the dipstick tube. If that's possibly leaking, replace the o-ring. You will need to unbolt the tube from the back of the engine - one of the bellhousing bolts holds the tube as you probably already know
The sleeve on the TQ sounds like it had a won hub and somebody stuck a sleeve over it. Personally, I think that if it's that worn, then the TQ should be replaced as I would suspect lotsa miles.
Leak possibilities in front - front seal, pump o-ring, or pump gasket. The front seal needs to be installed carefully and be sure that the little internal spring that goes around the inside to hold the rubber part is in place after you install it. It can get knocked out of place sometimes. As mentioned, the new seal needs to be lubed and installed straight. Also, wait until you are ready to install the tranny then install the TQ, don't stick the TQ in the unit and leave it hanging for a couple of days, it can distort the seal. Also, I know it sounds like a no-brainer, but be sure that you have the right seal for the application, you never know.
When you unbolt the front pump, there is a gasket that goes around the perimeter and there is a also a big 0-ring that goes around the circumference of the pump housing. The idea is that when you tighten down on the bolts, the o-ring wedges into place and the gasket seals off the back face of the pump housing. Both can be possible points of leaking, but both are very cheap in part cost, unfortunately lots of labor. However, if you have the tranny out anyway, it may be worth taking a close look to see if the leak is possibly coming from these.